Since 2014, our denim trade-up program has taken back more than 2.3 million pairs of jeans, giving them another life through resale, reuse or recycling. For Earth Month, we spoke with two people who live this idea every day—Stephan Brovko of Shop Denim Revival and Susan Lee of Wilder Los Angeles—shop owners who believe that clothes should be loved forever, kept in rotation and passed down for generations.

Stephan Brovko

Founder of Shop Denim Revival

On Stephan: Work Shirt in Japanese Chambray / The Vintage Tee / The 1991 Loose Straight Jean

MW: You spend your days surrounded by denim with history. What do you notice about the way great jeans age—and what makes a pair worth keeping alive?

Stephan Brovko: Personally, I think a great pair of jeans is one with a unique fade that tells a story. For example, an extremely old pair with strike marks on the back of the leg tells me that a rancher smoked and lit matches against their jeans. Similarly, a small tear in the pocket can show that someone carried a pocket knife there, or a square of fading might reveal a wallet carried in the back pocket. Things like this offer a peak into the past and how people used to live and do things.

Every pair is worth keeping alive, as long as you still find joy in wearing them.

MW: Vintage denim has already lived many lives before it reaches your shop. What do you love about the idea that clothes can keep moving through different people and eras?

SB: It’s amazing to see someone fall in love with something another person once abandoned or let go. Something that was left for nothing can be given a new life, bringing joy and happiness to someone else all over again.

In a sense, you’re wearing history. It reminds you that people in the past weren’t so different from us today.

MW: For someone building a wardrobe today, what’s your advice on finding denim that will actually get better with time?

SB: If you’re aiming to keep one pair for a long time, start with denim that’s as dark as possible. Wear the jeans consistently and watch the fades develop naturally over time. As you do, you’ll begin to see changes shaped by your daily habits, and in the end, the jeans will tell the story of your life.

Susan Lee

Founder of Wilder Los Angeles

On Susan: The Easy Shirt in Poplin / The Relaxed Tee in Vintage Jersey / Pieced Barrel Leg Jeans / The Oaklynne Sneaker / The Signature Woven Tote / Medium Silk Bandana

MW: You spend your days surrounded by denim with history. What do you notice about the way great jeans age—and what makes a pair worth keeping alive?

Susan Lee: Jeans are great storytellers. What gets me about a pair of vintage jeans every time is what they physically tell you about the life of the person who wore them: through the patina formed over time, the creases and whiskers, the highs and faded lows, every rip and tear and, of course, the softness that can only come from years of wear. Each pair tells a specific story, unique to both the jeans and the person who lived in them.

I also love that denim evolves over time. A great pair of jeans is like a painting that transforms through consistent wear; they’re worth keeping alive for that reason alone. You build a relationship with them—they grow older with you, evolve with you and become a piece of your art and a part of your story. That, to me, is what makes them worth keeping.

MW: Vintage denim has already lived many lives before it reaches your shop. What do you love about the idea that clothes can keep moving through different people and eras?

SL: First and foremost, I love the sustainable aspect of denim and clothing. By making garments last and recycling them—rather than disposing of them to sit in landfills—we reduce their impact on the earth we live on. This belief is the foundation on which Wilder Los Angeles was built.

My shop is also grounded in the core idea of style, not fashion. Fashion and style are two very different things. Fashion is like a pendulum, constantly swinging back and forth, while style is an anchor—it holds steady no matter where the pendulum swings. Great vintage clothing that moves through time speaks to style rather than fashion and will always stand the test of time.

MW: For someone building a wardrobe today, what’s your advice on finding denim that will actually get better with time?

SL: Make sure you choose denim that suits your personal style and not just current fashion trends. This is very important. Pay close attention to the details of how the denim is made, especially the fabric. A heavier-weight fabric will last longer and get better over time. And remember, great denim is an investment piece: it shouldn’t be cheap, it should be high quality. Invest in it, and it will last you a lifetime.

Right now, it’s woven leather.

Understated, but impossible to ignore. Textural without trying. The kind of bag that makes a white tank and straight-leg denim feel intentional. Polished, but not precious. It’s the bag you take to breakfast, to a 10am meeting, to a dinner that runs late. The one that works with tailored pieces or bare shoulders. With flats. With heels. With anything, really.

This season, we’re not saving it for summer—we’re taking it everywhere, starting now. And depending on the shape, it changes the mood entirely.

The Woven Shoulder

For the reliable one. Who knows your coffee order. And always keeps it together.

Outfit:
Vintage straight-leg denim. White ribbed tank. Oversized blazer. Sunglasses (the weather app says clouds, but the optimist in her is always ready for sun).

Where she went:
A 9am meeting that turned into a 12:30pm lunch that turned into “one quick stop” at the bookstore.

What she packed:
• Lip balm (or two, somehow)
• A notebook with exactly three good ideas in it
• Hand cream
• Sunglass case she never actually uses
• A protein bar she forgot about until 4pm

This is the bag that doesn’t overcomplicate things. It sits neatly on the shoulder, doesn’t fight your coat and understands proportion. Best of all, it makes denim feel intentional.

It’s structured but not stiff. Put together, without trying too hard.

The Woven Tote

She believes in being prepared. And she has the space to do it.

Outfit:
Relaxed button-up. Wide-leg trousers. Ballet flats. Hair in a low bun that took less than a minute.

Where she went:
Train ride into the city. Studio visit. Farmers market on the way home.

What she packed:
• Laptop
• Farmers market flowers
• A book she may or may not finish
• Reusable grocery bags (tote inside tote energy)
• Sunglasses, keys, wallet, snacks (just in case)

This tote is the overachiever. It fits everything without looking like it’s trying. The woven texture keeps it from feeling corporate—it’s soft utility.

She doesn’t say she has it handled. She just does.

The Woven Crossbody

She likes to keep her hands free. Emotionally and otherwise.

Outfit:
Cutoff shorts. Lightweight knit. Leather sandals. No plans, which is the plan.

Where she went:
Saturday flea. Ice cream. A long walk that accidentally became five miles.

What she packed:
• Card holder
• Phone
• Lip gloss
• A tiny sunscreen
• That’s it, that’s the list.

The crossbody is decisive. It edits. It eliminates. It refuses to carry what doesn’t matter.

It’s the one you reach for when you want to feel lighter—physically and otherwise.

The Woven Bucket

Quietly cool. Never asks for attention but gets it anyway.

Outfit:
Crisp poplin. Oversized sunnies. Sneakers.

Where she went:
Gallery opening. Low-key dinner with friends.

What she packed:
• Wallet
• Keys
• A small camera
• A folded-up cardigan “you never know”

There’s something about a bucket shape. It feels effortless. A little undone in the best way. The woven texture softens the silhouette, keeps it from feeling too precious.

This bag doesn’t try to be the moment—it just is the moment.

The Woven Zip Shoulder

The practical one who still has great taste.

Outfit:
Soft knit tee. Straight jeans. Leather loafers.

Where she went:
School pickup. Grocery run. Afternoon coffee. Life.

What she packed:
• Everything
• And it all zipped closed, too

This one is for movement. For full days. And for the people who carry their lives in their bags.

The zipper gives peace of mind. The weave gives personality.

There’s a strange tension in how we dress right now. We have more options than ever, yet we feel increasingly disconnected from what we wear. Creative references now come prepackaged, while trends move so quickly that style has less to do with personal choice and more to do with “fitting in.”

But when everything seems to be circulating all at once, how do you find out what really belongs to you? That’s where nostalgia enters the chat, flooding our newsfeeds.

Like those resurfaced pictures of JFK Jr. and Carolyn Bessette Kennedy, or photos of Tom Selleck and Harrison Ford in their absolute prime. People are hungry for moments they’ve never lived through.

And I can understand why. Because while the present feels commoditized and endlessly replicated, the past gives us clarity and context.

I feel the pull of nostalgia most when I’m getting dressed and not overthinking what I’m putting on. On days when I’m not trying to “look like” anything, I almost always reach for the same pair of jeans.

Denim makes this easy to see because it changes with use; it breaks in slowly, creases where you move and fades over time. Eventually, it stops feeling new and starts feeling like yours. But that’s not something you can rush or replicate, it only happens through wear.

Shaker-Stitch Full-Zip Sweater / The 1991 Loose Straight Jean

This is also where nostalgia can be misunderstood, because there’s a difference between pulling from the past and trying to recreate it exactly. When style turns into reenactment, it can feel stiff, like you’re wearing someone else’s idea.

The moments that work best are quieter.

Most people already have this kind of relationship with a few things in their closet without even realizing it. Pieces they keep around for reasons that are hard to explain, like a jacket that reminds them of a certain time, or a pair of shoes that are worn out but still preferred.

But the pieces that get the most wear are not often the ones that shout the loudest.

Ribbed Crew Socks / Linked Leather Belt

In a culture where everything is a remix of a remix, those small preferences matter—not because they’re unique, but because they’re specific. Over time, they shape how someone dresses without them even having to think about it. People often look at nostalgia and want what they see, without recognizing that what they see looks so good because it was lived in.

I think of refining one’s personal taste as an ongoing practice of saying “no.”

When I moved to New York almost 12 years ago as a freshman at FIT, I was eager to try on every aesthetic I encountered: boho like the Olsen twins; all-American like Ali McGraw; supersleek like the downtown moms I was babysitting for on the weekends. It was both exhilarating and exhausting to jump from persona to persona. What I aspired to most, though, was something steadfast—a way of dressing that felt entirely my own. Not because I wanted to stand out, but because I was tired of feeling like I was constantly performing someone else's idea of style.

Poplin V-Neck Shirt / The Perfect Vintage Wide-Leg Crop / Medium Silk Bandana / The Brioche Bag / The Dolli Glove Loafer

Experimentation is a necessary step along the way. But the ultimate goal, for me, has always been to be able to say, “I always wear this,” or “I never wear that.” That clarity—the ability to say no—is what cuts through the noise. Restriction is chic! And I’m always at my most creative with a little constraint.

So where does one begin the journey of personal style when we’re all exposed to the same trends on repeat? When every scroll serves up another microtrend—quiet luxury, mob wife, coastal grandmother—each one designed to make you feel like you’re missing out if you don’t immediately adopt it. I have a few ideas.

Nailing the base is step one. To do this, you need jeans that feel like you. And since you are not a mannequin frozen in time, this is an ongoing process. As someone who just gave birth, I can attest to the comfort of denim that meets you right where you are.

But here’s why starting with the basics matters: when you have a foundation you trust (jeans that fit, a white shirt that works, shoes that make you feel grounded) you’re less susceptible to chasing every trend that crosses your feed. The basics become your anchor. They’re what you return to when the noise gets overwhelming, or when you’re tempted to buy something just because everyone else is wearing it.

The key here is to be open-minded and to try things on in-person as much as you can. The Emmy Jean and I weren’t love at first sight. But after slipping them on with a plain white matching button-up, I felt the familiar sigh of relief that comes with discovering a sartorial base from which countless outfits will evolve. That’s what good denim does: it simplifies everything else.

Left: The Brioche Bag / The Emmy Wide-Leg Jean / The Mylie Ballet Flat

Right: Poplin V-Neck Shirt / The Perfect Vintage Wide-Leg Crop / Medium Silk Bandana / The Brioche Bag

When scrolling social, become a student of what, in particular, you love about an outfit you’re saving for inspiration. Is it the cut? The composition of the fabric? The way certain pieces anchor a look? This is how you sift through the clutter—by identifying what genuinely resonates with you versus what you’ve been conditioned to like because you’ve seen it a hundred times.

Personally, I found myself drawn to the way black flats kept appearing in outfits I loved, grounding even the most elaborate looks with something simple and classic. Once I recognized that pattern, adding this pair to my wardrobe was a no-brainer. It wasn’t about following a trend, it was about understanding what I’m consistently drawn to and letting that guide my choices.

The Easy Shirt in Tranquil Blue / The Easy Shirt in Cherry / The Emmy Wide-Leg Jean / The Camren Bag in Suede / The Mylie Ballet Flat

Taking new pieces out for a day in the life is the true road test of whether a style is destined for a forever place in your closet. This is where you learn what’s actually “you” versus what just looked good on the hanger or in someone else’s feed.

I wore this vintage-style T-shirt on a Monday, then on a Wednesday and then again the next week. I couldn’t get enough! That repetition taught me something: the pieces that earn their place aren’t the ones you save for special occasions, they’re the ones you reach for when you’re working from home or running to a quick dinner with a close friend. Real personal style is built on wardrobe workhorses, not show ponies.

Cashmere Sweater Tee / The Easy Shirt / Bootcut Track Pant / The Dolli Glove Loafer

And when you’ve said “no” and skipped the trend or abandoned the cart enough times, you’re ready for the freedom that comes from knowing yourself and how you like to dress. This practice of saying “no” gets easier the more you do it. I often ask myself: does this feel like me, or does it feel like someone I saw on Instagram? Would I wear this if no one else was going to see it? Does it work with what I already own and love?

Once you’ve built that muscle, you can recognize your actual preferences instantly. Sweatpants—fashion-y sweatpants, to be specific—have been a staple in my closet since middle school. This pair has completely changed my airport ensemble. The best part is I can slip on a cashmere T-shirt once I land, tie a scarf around my neck and feel polished for a day of meetings. That’s the payoff: when you know what works for you, getting dressed becomes effortless instead of overwhelming.

So, the next time you're in a personal style slump, make a list of everything you don't wear: the cuts you avoid, the colors that never felt right, the trends you skip. You might just be surprised by how much clarity comes from identifying what you're saying “no” to. Because in an era of endless scrolling, where we're all exposed to the same things on repeat, your taste isn't defined by what you buy; it's defined by what you refuse. That's how you cultivate something that feels genuinely yours. And how you protect your style from becoming a carbon copy of everyone else's feed.

We sat down with our stylists to talk a little more about how great style isn’t about looking perfect, and why standing out and trusting your instincts are key.

Colorblocked Quarter-Zip Sweater / Smocked-Waist Midi Skirt / The Hester Flat

Shaker-Stitch Full-Zip Sweater / The Vintage Pocket Tee / Linked Leather Belt / The 1991 Loose Straight Jean

The Effortless Formula

Getting dressed shouldn’t feel complicated—in fact, we think it should feel effortless. Part of that mindset means eliminating the urge to chase trends, follow rules and, ultimately, letting go of perfection. For Senior Men’s Stylist Brendan, that’s where things get interesting.

“Imperfection feels more human. A little friction makes it personal,” he explains. He adds that when everything lines up just so, it can feel overly considered, stripping away the character that makes an outfit feel like you.

Low-Slung Baggy Jeans / The Dolli Glove Loafer / The Relaxed Tee / Roll-Top Ankle Socks

So, what’s behind an outfit that looks easy yet interesting? Start simple, then disrupt it—just a little. Senior Women’s Stylist Lauren approaches it by starting with a familiar base like jeans and a tee. She then introduces one element that feels slightly off.

“That way your outfit doesn’t feel too formulaic,” she says. The idea reinforces the notion that an element of unexpectedness brings personality into the mix.

Shaker-Stitch Full-Zip Sweater / The 1991 Loose Straight Jean / The Vintage Pocket Tee / Fatigue Pants

This “off” element also doesn’t need to be too loud. Subtly mixing sporty pieces with elevated ballet flats instead of sneakers results in a look that feels intentional (but not predictable) and soft (with an edge).

Colorblocked Quarter-Zip Sweater / The Brioche Bag /Smocked-Waist Midi Skirt / The Hester Flat

Brendan takes a similar approach for men’s, but with more restraint. Instead of adding pieces, he focuses on making sure at least one piece feels unplanned, knowing that a proportion, texture or detail can easily shift the balance into more interesting territory. From there, it’s the finishing touches that truly make an outfit yours.

Lauren explains, “Adding a favorite belt, or a shoe in an unexpected color or material—something worn and personal—keeps the outfit from feeling like a basic look anyone could wear.”

Brendan agrees, noting that repeating certain styling habits, like how things are cuffed, worn in or slightly imperfect, can sometimes have the biggest impact of all. Ultimately, effortlessness isn’t about doing less—or even more—it’s about doing what feels most like you.

Bleecker Sunglasses / The Slim Straight Jean / Button-Up Shirt / Chore Jacket

Rules Are Meant for Breaking

Once upon a time, fashion rules were relevant and even necessary, but those days are over. One obvious example is wearing white after Labor Day.

“You can wear white denim any time of year,” Lauren confirms. “I especially like wearing it in the winter.” For her, white jeans are a great foundation for any outfit and serve as a sort of blank canvas for your wardrobe.

Brendan agrees, “I like to start with an ecru bottom as a base, then create interest with color on top.”

The Canvas Utility Pant / Denim Type 2 Trucker Jacket / The McCarren Field Hoodie / The Rockaway Tee

Beyond that, personal style shouldn’t be about following rules anyway. Why not mix black and navy, or let your belt and shoes clash?

“In general, I do feel like there are truly no rules in fashion or style.” Lauren says. She adds, “There’s always an exception.”

The Emmy Wide-Leg Jean / The Oaklynne Sneaker / The Relaxed Long Sleeve Tee / Chunky Oval Chain Necklace / Semiprecious Cherry Charm / Pieced Fish Charm / Celestial Heart Charm / Semiprecious Strawberry Charm / Semiprecious Snail Charm

Finding Your Personal Style

Rome wasn’t built in a day—neither was personal style. It comes from years of experimenting, observing and applying everything you’ve learned to your own closet. The best way to find it?

“Just try on everything,” says Lauren. That includes trying pieces you don’t necessarily think are for you, like the colors you avoid, the silhouettes you’ve already ruled out—those are all fair game.

“And don’t be married to your usual size either,” she adds. So the next time you’re in a dressing room, why not go up a pant size, try a shrunken cardigan or experiment with a pattern that you never thought was very “you.” The outcome just might surprise you.

The '90s Boatneck Tee / Domed-Buckle Belt / The Emmy Wide-Leg Jean / Pointelle-Knit Cardigan

The Madewell Way of Dressing

By now, you’ve probably realized we don’t care much for perfection. We prefer clothes made for real life, styled in ways that feel instinctive—not contrived. There’s something about adding that slightly “off” element that keeps a look from feeling too polished or predictable. In theory, mixing different patterns shouldn’t work, yet somehow it does. Wearing white after Labor Day used to be a fashion faux pas, but now it feels fresh. And pairing pieces you wouldn’t normally put together feels unfussy and cool.

As Lauren puts it, “There’s a collision there. It doesn’t feel too spot on.”

The truth is, the outfits that feel most like you rarely follow any rules. How could they, when those rules were never designed with individuality in mind? The best outfits are the ones that feel a bit wrong, but also completely and totally right. Because getting dressed isn’t about perfection, it’s about getting personal.

Jordan is wearing the The Boxy-Crop Tee in Soft Slub and The Lexington Small Tote.

Tonight, I will be hosting an intimate gathering on behalf of Seen Library with Madewell—an evening centered around books, conversation and connection. When I officially started Seen Library in 2021, that’s exactly what I wanted to do: create space to slow down, share stories and simply be in the presence of friends, or even strangers. I’m so excited to do just that with a brand I’ve loved and worn for years.

I’ve been hosting Seen Library gatherings for over five years now and even back then, my friends and I were already spending so much of our lives online, whether for work or for fun. I began longing for simpler things from the past: holding a physical book in my hands instead of holding a phone, speaking to people face-to-face instead of through a screen, taking part in conversations without distraction. With so much of our lives now happening on our phones, it was important to me to bring people together around something that can only be felt and experienced in person. Now in 2026, that craving for in-person connection and intimacy has only grown stronger and more important than ever.

Seen Library events feature books wrapped in paper with only a few clues, inviting readers to choose their next read blindly.

Books have always felt like the perfect vehicle for this. The wrapped “blind date with a book” idea isn’t a novel one, but once I started incorporating it into gatherings, I wanted to take it a step further as a way to encourage conversation. Each book is hand‑wrapped in paper so that participants won’t judge it by its cover. Instead, they choose a book based on three clues, which I handwrite on a custom Seen Library card.

The clues might include the book’s genre, themes, setting or even how it might make you feel while reading. The third one is always a compelling quote from the book itself. These insights offer a small glimpse into the story under the wrapping and serve as talking points during the discussion. As part of the gathering, everyone shares why they chose the book they did based on which clues resonated with them the most.

That’s when something special happens. People begin to share a bit about themselves they might not have otherwise. They feel a sense of safety and comfort in opening up, because they see a part of themselves in the book they selected. Often, it’s through this simple exchange that vulnerability emerges and with it, genuine connection.

That’s where the name “Seen Library” comes from. In the pages of our favorite books, we’re invited to see and understand ourselves more clearly, as well as step into the perspectives of others.

For each gathering, I curate the book list and evening around a central theme. Tonight’s theme is A Return to Ease. With that in mind, I put together nine books that you can fall into easily yet continue thinking about long after the last page. From well-loved classics that nod to the past to contemporary novels that feel timeless, thoughtful and a bit unexpected, these picks are effortless reads to dive into as you begin a new chapter.

1. A Place for Us by Fatima Farheen Mirza

2. Beautiful World, Where Are You by Sally Rooney

3. Just Kids by Patti Smith

4. Kitchen by Banana Yoshimoto

5. Red at the Bone by Jacqueline Woodson

6. Sula by Toni Morrison

7. The Stationery Shop by Marjan Kamali

8. Tuesdays with Morrie by Mitch Albom

9. What You are Looking For Is in the Library by Michiko Aoyama

At its core, Seen Library gatherings celebrate individuality, creativity and connection. They’re about bringing people together in a way that feels natural yet deeply personal. It’s an experience meant to be felt, shared and remembered—just like a good book.

People love to hate January. Personally, I like to lean in hard. It’s my birthday month, so maybe that has something to do with it, but I relish the quieter pace January brings, as well as the opportunity to both hibernate and be productive all at once. January is a bit like those tape-up, tear-off flyers; it’s a month where you really can take what you need. Whether that means time to rest and recuperate after the holidays, or creatively reset and restart from the moment the clock strikes midnight on New Year's Eve, January offers the space to do either or both. For me, it’s usually the former. I use this time to take things pretty slow, which genuinely feels productive to me; after all, we all know you can’t pour out of an empty cup.

Denim Oversized Shirt-Jacket / The Relaxed Tee in Vintage Jersey / The Jules Slim-Straight Jean / The Mylie Ballet Flat

There aren’t any mad detoxes or extra hours at the gym, but there is plenty of cleaning, clearing, writing, sparking ideas, dreaming up plans, lighting the fire, finishing books started over Christmas, cooking from scratch or just watching four episodes in a row. January is when I ground myself and get ready for the next 11 months. After the frenzy of December, the slower pace of a new month feels almost essential. I’m an introvert at heart, but my job keeps me out and about a lot, so I love January for being the ultimate mental recharge. My dog Finn and I take lots of long walks, catching up on audiobooks and podcasts while I try to use the time to reflect on what I want from the year ahead and be thankful (or say good riddance!) to the year before.

What I wear has always had a big effect on my mindset; I think that’s why I wanted to work in fashion in the first place. I’ve always loved the transformative power of clothes and playing dress up. And it’s not just about what you’re saying on the outside; what I wear so often dictates how I feel on the inside, even if I'm not leaving the house. After over a decade of working from home, I’ve learned that finding a balance between comfortable and not feeling like you’re wearing pajamas is key. This time of year is no different; I want to feel like I'm up and about but still cozy and relaxed.

Chunky-Knit Alpaca-Blend Turtleneck / The Jules Slim-Straight Jean / Striped Camp Socks

Soft denim you can actually curl up in, and knitwear that’s cozy but more refined than loungewear are my go-to uniform for these in-between days, staples that feel ready for the day but still conducive to hibernating and saying no to plans. Thick socks or easy slip-on flats (honestly, shoes really help with concentration when working from home!), classic leather belts and a few simple metallic accents are the extras I lean on to take the simplest of pieces to a more elevated place. I don't want to have to overthink what I’m wearing, but I do want to feel good in myself, and these comfortable, everyday essentials tick all the boxes for the yo-yoing between brainstorming and vegging out that the new year brings.

Rib-Stitch Crewneck Sweater in Cashmere / The Dean Easy Straight Jean in Airy Denim / Oval-Buckle Belt / The Meadow Whipstitched Driver

Teagan T.

Influencer & Community Manager

What I’m buying in 2026:

1. Easy Crewneck Long-Sleeve Tee

2. The Idris Ankle Boot

3. The Wide-Leg Pant in Corduroy

4. Demi-Fine Mixed-Metal Stacking Ring Set

5. Knit Scarf in Wool Blend

6. Chunky-Knit Alpaca-Blend Turtleneck

7. Drop-Shoulder Polo Sweater in Merino Wool

My 2026 style resolution is: To build my wardrobe with intention and style with purpose—looking at the pieces I’ve cultivated over the past few years and doubling down on their style-ability. I want to push myself to pair items together that I might have otherwise overlooked, leaning into layering and unexpected color combinations.

Three words to describe my style: Intentional, playful, proportional.

How I’ll style these pieces with my wardrobe/things I already own: I envision pairing plush textures with pieces that are more tailored or fitted, or mixing a tomboy-esque striped long-sleeve with a feminine poplin skirt. Black boots are also a staple in my winter rotation; I like styling pointed-toe pairs with wide-leg trousers for a sharp contrast, or with a long silk skirt and blazer.

My non-negotiables when buying a new piece: I have to be able to visualize at least three different outfits with said piece. There has to be something noticeably different from other items I own (for example, if it’s a black skirt, is there a difference in texture or material?). The quality needs to feel substantial. And, lastly, it has to get me excited!

The best style advice I ever got/heard is: Don’t be afraid to play with color, texture and pattern.

Virginia T.

Associate Copy Director

What I’m buying in 2026:

1. The Balloon Jean

2. Semiprecious Signet Ring

3. Reversible Denim & Sherpa Jacket

4. The Grayson Penny Loafer

5. Raglan-Sleeve Sweater in Stripe

My 2026 style resolution is: To have more fun with color and details. I tend to go for classic silhouettes and clean neutrals, but lately I’ve been exploring new textures from fuzzy yarns to faux fur, unexpected colors and playful statement accessories. In the new year, I just want to get more experimental.

Three words to describe my style: Timeless, fit-focused, meticulous.

How I’ll style these pieces with things I already own: My current closet is a mix of new classics and a lot of vintage, and the beauty of these five pieces is that each feel unique on their own, but are also versatile enough to seamlessly slot right in.

They touch upon the elements that make a good outfit even more interesting, like the touchable coziness of sherpa or the exaggerated cut of the Balloon Jean.

My non-negotiables when buying a new piece: First and foremost, I have to feel good as soon as I put it on; I shouldn’t have to fuss with it or over-style it to make it work. Also, if I can imagine myself still wearing it in a few years—both in style and quality—then it’s a winner.

The best style advice I ever got/heard is: Fit and craftsmanship are everything.

Sophia J.

Social & Community Coordinator

What I’m buying in 2026:

1. Oversized Pullover Sweater

2. Lace-Trim Square-Neck Tank

3. Chunky-Knit Alpaca-Blend Turtleneck

4. Organic Cotton Bandana

My 2026 style resolution is: To play dress up instead of simply getting dressed. I’m a fool for a good tee, ballet flats and a perfectly worn-in pair of jeans—it’s easy to throw on when I’m rushing out the door (as I often am). But this year, I want to practice giving myself the time to play around with my closet and get creative.

Three words to describe my style: Laid-back, a bit bohemian and a bit mod.

How I’ll style these pieces with things I already own: The sweater will become my go-to cozy piece for throwing on with jeans in winter. I’ll style the lace-trim tank under my favorite navy blazer with jeans and some fun heels. The turtleneck will look great with a mini skirt and a pair of tall boots. And I’ll wear the bandana in my hair, on my bag, around my neck, through a belt loop or two, etc.

My non-negotiables when buying a new piece: Longevity—in both quality and style. At least 70% of my wardrobe consists of my mom’s old clothes that have held up over the years. I want to build a closet that lasts and can be passed on.

The best style advice I ever got/heard is: I’m not sure who said this, but I’ve always liked this quote: “People will stare. Make it worth their while.”

Shay G.

Copywriter

What I’m buying in 2026:

1. Chunky-Knit Alpaca-Blend Turtleneck

2. The Easy Shirt in Poplin

3. Lace-Trim Square-Neck Tank

4. Ribbed Ankle Socks

5. Rib-Stitch Crewneck Sweater in Cashmere

My 2026 style resolution is: To finally get rid of what I don’t wear and replenish with high-quality, versatile pieces that I know I’ll return to for years to come.

Three words to describe my style: Coastal, classic, undone.

How I’ll style these pieces with things I already own: I love nothing more than an oversized poplin button-up—it’s easily the most versatile piece in my closet. The Cashmere Pullover will morph from a sweater into a scarf when I need it to, while the Chunky Alpaca Turtleneck (sized up, of course), will work as a very cozy top for chilly office days or a mini dress when off-duty, paired with knee-high boots.

My non-negotiable when buying a new piece: I always ask myself if I am buying something because it reflects my style, or if it’s because I see other people wearing it. If it’s the latter, can I put my own spin on it? If not, it’s probably not worth the buy.

The best style advice I’ve ever heard is: I want my pieces to feel lived-in and generally refuse to be precious with my clothing. That’s my unsolicited advice: wear your clothes, often and well.

Lilian P.

Director, Brand Creative

What I’m buying in 2026:

1. The Dean Easy Straight Jean

2. Zip-Front Mockneck Cardigan

3. The Dimes Kitten-Heel Boot

4. The Mylie Shoulder Bag

My 2026 style resolution is: Build a year-round wardrobe that can transition from season to season.

Three words to describe my style: Classic, uniform, denim-centric.

How I’ll style these pieces with things I already own: I’ll pair the denim with staples like my hand-knit wool sweaters and my go-to Chanel ballet flats. As for the jacket, I’ll style it with the black jeans that I got from my mom—she’s had them since the ‘'80s and passed them down to me.

My non-negotiables when buying a new piece: There are two things I look for when buying a piece: timelessness and quality. I like to wear things over and over, so I need to make sure it will last for a year or more. I’m not a trend follower—I prefer classic staples.

The best style advice I ever got/heard is: Make sure you can see yourself wearing it more than 30 times.

I’ve spent 18 December 31sts in New York City (give or take an abscondment to warmer climes), and when I think about previous New Year’s Eves, the memories have an astigmatic glitter and a fuzzy, velvet touch. I don’t remember much about my outfits, but I do remember all of the champagne and kissing, and how absolutely frigid it was in sheer tights and heels. These recollections are from the earlier days, in my 20s, at college, traipsing from one party to the next, racing against the countdown to midnight; a tangle of legs and fur.

For the last few New Year’s Eves, I’ve started the evening at my friend’s cozy house, pasting vision board assemblages ripped from magazine editorials. We never have enough glue sticks, so there’s sharing and waiting and chatting and wine; all of this is part of the ritual. There’s also a beautiful cake and armchair psychoanalyses of our boards at the end. We’re envisioning: who will we be in this coming year? What do we want to evoke? We’re asking through pictures: how can I be better?

The reflection reflex that comes with the end of a calendar year needn’t be complicated or heavy. It’s like a second birthday for everyone: a time to assess and use our 20/20 hindsight to push forward productively, collectively. Making room for contemplation and practicing versatility are paramount in a hectic world. And—because this essay is about getting dressed—how do we communicate this to the stranger passing us on the street, both of us on our way, in our own way, to celebrate a year gone? If we want to convey that moving forward, we’re going to be more thoughtful, more content, less needlessly reactive.

Left: Textured-Stitch Crewneck Sweater in 100% Cotton / Easy Y-Neck Button-Up Shirt in Corduroy / The Vintage Flare Jean / Medium Silk Bandana / The Emilie Glove Pump

Right: Chunky-Knit Alpaca-Blend Turtleneck

It won’t be with too-short, too-tight dresses we’re tugging down all night and it won’t be with lips blue from the cold and goosebumped arms. A very Madewell NYE outfit is cozy, easy: tailored denim, a very good sweater, an excellent coat (or two) and a hint of glamour in our accessories. Everything can be worn multiple ways. Leaning on the idea that good stuff lasts, we’re saying we look fantastic, but not impractical. The confidence that comes from comfort is palpable and truly functions as part of the outfit itself.

Chunky-Knit Alpaca-Blend Turtleneck / Sculpted Cutout Brooch / Johnny-Collar Sweater in Merino-Silk Blend / The Jules Slim-Straight Jean / The Emilie Heeled Mule

After the vision board analysis, I go out and look for the party. Balance is important here, but dressing for this dichotomy is actually quite easy. I’m not suggesting we circumvent the ball drop costume spectacle, but I am offering an alternative: ease and longevity, comfort and celebration. The culmination of a year is an important commemoration—codifying what we’ve learned, who we hope to become. All that growing we did over the last 12 months (18 years?) can be shown in a few pieces expertly layered.

As someone who will be sitting on the floor, gluing my future onto poster board and then heading into the night to find a little glitter, plant a kiss, hug my friends who have been my friends since we were teenagers, I play the long game with my outfit for the night. The heel can be high, but must be walkable as I take particular umbrage with the inevitable Uber surge pricing. Pants are better for sitting cross-legged and a coat over a coat says: “I know who I am, and I do not like to sacrifice my body temperature for fashion.”

Left: Textured-Stitch Crewneck Sweater in 100% Cotton / Easy Y-Neck Button-Up Shirt in Corduroy / The Vintage Flare Jean / Medium Silk Bandana / The Emilie Glove Pump

Right: Russel Oval Sunglasses / Knit Bandana / Alexa Chung for Madewell Charlotte Satin Camisole / Oversized Button-Up Shirt / Double-Faced Brushed Long Coat / Single-Breasted Topcoat in Suede / The Mylie Shoulder Bag

Some ground rules for New Year’s Eve outfits, and good times that I’ll be abiding by:

A red lip is always festive, and NYE is a collective rejoicing if you find the right crowd. Layers allow for texture play and stripping when the room gets too hot (a marker of a good party). A fur coat (faux or otherwise) is always a good idea when the weatherman is touting, “Today feels like five degrees, folks!” Considered and joyful are not mutually exclusive descriptors, and red is a celebratory color that adds oomph to an outfit—even in a sweater slung about the shoulders. Hang out with the friends that make you belly laugh. Kiss everyone.

Chunky-Knit Alpaca-Blend Turtleneck / The Jules Slim-Straight Jean

And, for that aforementioned long game, remember: a popped collar changes a shirt’s casualness. Scarves are versatile and warm (sweaters can be scarves too—just use the arms), diamonds (faux or otherwise) enhance the allure of it all. And finally, resolve to have a good time in clothes you love, feel good in and will wear for years and years to come.

Russel Oval Sunglasses / Demi-Fine Bezel Large Drop Earrings / Knit Bandana / Alexa Chung for Madewell Charlotte Satin Camisole / Oversized Button-Up Shirt / Double-Faced Brushed Long Coat / Single-Breasted Topcoat in Suede / The Mylie Shoulder Bag / The Greta Ballet Flat

Annual rituals and family rhythms are often at the heart of the holidays—especially for Justin Boone and Telsha Anderson-Boone. Based in Chicago, the creative couple stays busy balancing work and life while raising two kids under two. Telsha is an entrepreneur and creative director, while Justin works as a menswear stylist, designer and creative director—yet both approach the season the same way they approach style: with intention.

We sat down with the tastemakers to talk about the traditions they’re carrying forward, the new ones taking shape and how their style has evolved since becoming parents. From nap-time in front of The Grinch to snow days in matching pajama sets, here’s what’s bringing them joy right now.

MW: What are your favorite holiday traditions to do with the kids?

Justin: My favorite holiday tradition is spending the entire day in the house with movies and our son Shepherd’s favorite car toys. Our daughter, Seona, isn’t quite old enough to have any favorite toys yet, so I enjoy watching her crawl around and learning her boundaries with all of the holiday decorations.

Telsha: Mine is snuggling up on the sofa and taking family naps while the cartoon version of the Grinch plays in the background.

MW: Are there any new traditions you’ve started since becoming parents?

Telsha: One of our favorite traditions is passing down the ones we’ve been given from our families and teaching the kids the importance of each one! Things like baking, going to see the official Christmas tree in the nearest major city or spending a snow day in matching pajamas.

On Telsha: Flocked Denim Chore Jacket / The Cleo Straight Jean / The Remy Mary Jane Flat

On Justin: Ribbed Beanie / Crewneck Sweater in Heritage Merino Wool / Open-Collar Sweater Polo in Yak-Alpaca Blend / The 1991 Loose Straight Jean / Ribbed Crew Socks / Paraboot Chambord Leather Derby Shoes

MW: Any tricks for staying comfortable, but still feeling put-together?

Justin: Function over fashion is always a win in my book. Finding ways to layer while still being intentional so that the fit still has dimension, even as each layer comes off.

Telsha: When in doubt, overdress.

MW: Tips on dressing up denim for the holidays?

Justin: My absolute favorite way to dress up denim is by pairing it with a great sweater. I like layering multiple sweaters or styling an extra one draped over my shoulders.

On Justin: Patch-Pocket Shirt-Jacket in Wool Blend / Twill Shirt-Jacket in Broken Plaid / The 1991 Loose Straight Jean / Ribbed Crew Socks / Paraboot Chambord Leather Derby Shoes

On Telsha: Bar Chain Tennis Necklace / SoftWool Boxy Crewneck Sweater / Pieced Barrel-Leg Jeans / The Mylie Shoulder Bag / The Elevated Collection Sculpted Stacking Ring Set

MW: How would you say your style has evolved since becoming parents?

Justin: I’ve naturally phased out most of my delicate clothing and stick to only wearing pieces that I’m comfortable rolling around in the dirt in.

Telsha: I always gravitate toward what I can do multiple things in. From the park with the kids to drinks with the girls, my outfits have to evolve throughout the day while still making a statement that’s true to my personality.

MW: What’s your go-to outfit formula for days spent mostly at home with the kids?

Justin: A great pair of sweatpants or my favorite pair of jeans with a T-shirt or hoodie.

Telsha: High-waisted jeans and a cozy sweater!

On Telsha: SoftWool Boxy Crewneck Sweater / Pieced Barrel-Leg Jeans / The Lexie Ankle Boot

On Justin: Ribbed Beanie in Heritage Merino Wool / Patch-Pocket Shirt-Jacket in Wool Blend / Twill Shirt-Jacket in Broken Plaid / The 1991 Loose Straight Jean / Paraboot Chambord Leather Derby Shoes

MW: What does downtime look like for your family during the busy holiday season?

Justin and Telsha: Funny enough, we often start off separately in small pockets of the house, only to find our way back next to each other. All four of us are like little magnets.

MW: Describe what the “perfect day” looks like for your family this time of year.

Justin: We’ve had quite a lot going on this year. Right now, the perfect day consists of stillness with some home-cooking and jazz music playing in the background.

Telsha: Quiet time! Little giggles! Sparkly Christmas lights.

MW: Do you have any tips for keeping the holidays feeling calm instead of chaotic?

Justin: It’s all about the small moments. With children, things are destined to get chaotic every once in a while, so it’s best to focus on all the small wins.

Telsha: Do whatever makes you happy! Whatever keeps a smile on your kids’ faces. After all, the holidays only come once a year.

The year is 2013.

I’m in my freshman year of college, at a small liberal arts school where all the girls wear Birkenstocks and that one American Apparel sunflower-print smock dress (you know the one). “Personal style” is not a phrase that has entered the cultural lexicon yet, but the general ideas were swirling around in my mind. I knew that I cared about clothes more than the average person—and that I really wanted to figure out what my “look” was.

One day, I was hanging out at a friend’s dorm when a ballet pink book on her shelf caught my eye. The cover had a one-word title—IT—in all caps. Above it floated the name Alexa Chung, spelled out in that lowercase loopy cursive font that was popular in the 2010s. My friend, sensing my intrigue, lent it to me. At the point, I had a loose awareness of who Alexa Chung was from my teenage Tumblr dabblings: British model with a Chinese last name, poster girl for curtain bangs, muse behind several Arctic Monkey songs…

But it wasn’t until I finished IT, her collection of essays, photographs and artistic musings, that I truly came to appreciate her as a multifaceted fashion girl: she’s extremely witty and curious about the world; she laughs easily and is not afraid to cut her own bangs on Zoom! It’s these qualities that make her so charming—it’s why she can look cool in anything, even a potato sack.

The year is 2025 and I still feel like I’m growing up with Alexa Chung

Just last week, I listened to her Fashion Neurosis podcast episode with Bella Freud. I thought, “Ugh, I could just listen to her talk for hours.” The way she describes her outfit as treading the balance between “perverse and joyful” gives me the language to pinpoint what I am forever trying to cultivate in my own style.

On Monday, Madewell launched their new collaboration with Alexa Chung. The collection is inspired by Alexa’s signature preppy, tomboy-meets-vintage feminine aesthetic.

Below, I style eight looks based on my favorite pieces.

The Slip Dress

Courtney Satin Slip Dress / Floral Brooch / Shopper Tote

When I think of Alexa’s quintessential looks, a lacy, vintage slip dress is high up there on the list. This dress offers a fresh interpretation that I styled with a floral brooch pinned in the center of the bust.

The Striped Shirt

Lou Poplin Shirt / Vivienne Leather Wrap Skirt / Skinny Scarf / G.H.BASS Loafers / Bucket Tote

Alexa LOVES her striped shirts. If you read any magazine article that breaks down how to get her look, I guarantee you there will be a collage of her in Breton boatneck tops and colorfully striped, mohair jumpers.

This shirt is a classic button-up with a little buttoned pocket on one side—very much aligned with Alexa’s tomboy sensibilities. The stripes are a warm, rusty red, perfect for autumnal color layering.

The Baby Blue Cami

Charlotte Satin Camisole / Mick Satin Track Pant / Studded Leather Belt / Bucket Tote

What is it about this particular shade of vintage baby blue that evokes such nostalgia? I love how it looks against the white lace trim—delicate and dainty.

You might be familiar with the concept of styling a tiny top with big pants. It’s a tried and true formula, but I added a twist on the proportions with this studded belt.

The Leather Skirt

Vivienne Leather Wrap Skirt / V-Neck Baby Tee / Suede Topcoat / Bandana

Black leather is classic Alexa: gritty, edgy, a little rock and roll. The length of skirt makes it polished enough for the office, but the metal ring hardware keeps it from feeling stuffy. You can also hang accessories from it! I went with a pomegranate-colored bandana, but a carabiner keychain or chunky charms would be just as cute.

Admittedly, I don’t wear a lot of black, but when I do, I like pairing it against a cherry red for high color contrast. The chocolate brown suede coat works as a third element to soften the lines and pull everything together.

The White (Nonbridal) Dress

Courtney Satin Slip Dress / Bandana / G.H.BASS Loafers / Suede Shoulder Bag

I feel like there’s a cultural aversion to wearing long, white dresses out of fear that it reads overly bridal. Which is honestly such a shame because as the proud of owner of three cream-colored slip dresses—they’re some of the most versatile pieces in my wardrobe! This dress reflects light so beautifully and makes me feel like a marble statue.

How I’d dress it down: bandana in the hair, which gives it an earthier vibe, and a dressy loafer instead of heels.

The Sporty Track Pant

Lou Poplin Shirt / Mick Satin Track Pants / G.H.BASS Loafers

We can’t talk about tomboy style without mentioning track pants! Whenever your outfit feels too put-together, too stiff, too flat, slip into a pair of relaxed track pants and let the magic happen. These come in a versatile, navy color, with a red stripe down the side.

These would make for a great airport pant, by the way.

The Ultralong Skinny Scarf

Skinny Scarf / Suede Topcoat / Vintage Flare Jean / Studded Leather Belt / Bucket Tote

I associate these super long, striped, Very Hungry Caterpillar-type scarves with the 2000s. They’re famously more decorative than functional and that’s part of the appeal—it’s like jewelry in knitwear form.

They also infuse your outfit with movement, a touch of levity amidst the heavy coats of colder months. I styled mine on top of a suede topcoat and flared jeans for an eccentric, librarian vibe.

I actually pray for gusts of wind when I’m wearing a long scarf because the way it cascades in the wind brings a certain runway-esque DRAMA!

The Floral Pin

Lou Poplin Shirt / Studded Leather Belt / Floral Brooch / Vintage Flare Jean / Shopper Tote

Finally, the most Alexa accessory might just be a floral brooch.

There’s this photo from 2016 where she’s wearing a white camisole, cropped cigarette jeans, a shrunken, black velvet blazer and a robin egg’s blue floral brooch pinned on the lapel. It lent an air of whimsy and romanticism to an otherwise simple outfit.

Once you start adorning your clothes with a floral brooch, it’s hard to stop. You can pin it over a pocket, over a button, on the side of a waistband…the possibilities are endless!

Thanks for reading! I’d love to hear about the Alexa Chung outfits that live rent free in your mind.

This year for the women in my life, I’ll be gifting jewelry—specifically personalized chains and charms that remind me of each of them, whether it’s a memory, something we share or something special to us both. I take a lot of pride in my gifts, so I was especially honored to get a first look at Madewell’s new charm collection to choose pieces for loved ones.

I spent a few days with Madewell’s new jewelry, and not only do the pieces feel incredibly elevated, but I also found myself not wanting to take them off. The charms are whimsical yet sophisticated, dainty yet detailed, making them the perfect choice for a gift that feels thoughtful and personal.

Without further ado, here are six of my favorite Madewell pendants—and who I’ll be gifting them to this year:

Bar Link Watch Chain Necklace / Freshwater Pearl Flower Charm / Semiprecious Mariner Link Charm

For My Best Friend:

Finding the right gift for my best friend can be tough. She loves all things vintage and is still refining her jewelry style, so I wanted to give her something she could wear every day and feel beautiful in. This watch chain necklace is perfect—she can dress it up with charms or keep it simple on its own. For the charms, I chose this clover-inspired one for luck, since she’s beginning a new chapter in her life and career, and the mariner link to symbolize our bond (we’ve been best friends since meeting at a Bar Mitzvah when we were 11!). It’s always hard to find the right gift for someone who means so much, but I’m excited to give her something personal that she can wear in a multitude of ways. Plus, she deserves it!

Chunky U-Link Chain Necklace / Semiprecious Olive Charm / Chunky U-Link Chain Bracelet / Semiprecious Apple Charm

For My Mom:

Since I just moved to NYC, I thought it would be nice to gift my mom a few pieces that could help her feel more connected to the city. This is my first time living away from Los Angeles, and I’ve been counting down the days until I can bring her to Bemelmans Bar (my favorite bar in NYC) so we can sip their famous martinis together. The olive charm felt like the perfect way to mark this new chapter—for both of us.

We share a love of jewelry (I definitely get my love of shiny things from her), so I know she’ll absolutely LOVE this combination. While I typically gravitate toward simple, everyday pieces, my mom has always loved charms. She began collecting them back in the Juicy Couture days (who remembers those charms?), so I know she’ll appreciate something that feels so special to both of us—and the memories we’ll make while wearing our pieces.

The apple charm was another perfect pick to represent “the Big Apple.” It also reminded me of the Moschino charm bracelet with oversized fruit charms she used to wear when I was growing up. There’s something so nostalgic about a charm bracelet, and I love that they’re making a comeback—a reminder that great jewelry never goes out of style.

The Essential Zip Card Case Wallet / Semiprecious Mariner Link Charm / Chunky U-Link Chain Bracelet / Horseshoe Charm

For My Equestrian-Obsessed Cousin:

I mean, who doesn’t love an equestrian theme? I’ve always been drawn to horseshoe jewelry—I just think they’re so special, especially this piece. My cousin started riding when she was five and has collected countless equestrian-themed objects over her 15 years of riding. But when I think about her jewelry, she doesn’t really have anything that reflects her personality or interests. That’s why I thought this horseshoe charm was the perfect choice—it captures who she is, along with her love for horses and riding. I’m also adding a patent leather wallet for her, complete with an extra charm—because you can never have too many!

Chunky U-Link Chain Bracelet / Freshwater Pearl Flower Charm

For My Partner’s Mom:

Every holiday, I add to my partner’s mom’s jewelry collection. She’s amazing, and I think she deserves the world. She never really splurged on jewelry for herself, so my partner and I have made it a tradition to expand her collection through gifts over the years. She has refined taste, gravitating toward simple, sophisticated clothing—and her jewelry always reflects that.

For a long time, she stuck to the same pieces, like her classic gold hoops, until a few years ago, when we upgraded them to diamond hoops, which she now wears all the time. I truly believe you can never give too much sparkle—every woman loves a little shine—so every chance I get, I spoil her with something beautiful.

This year, I decided on the clover flower charm bracelet for her. She doesn’t have any bracelets she wears regularly, so this one felt like a good fit—it’s delicate and elegant, just like her.

Bar Link Watch Chain Necklace / Freshwater Pearl Flower Charm

For My Childhood Friend:

There’s nothing I love more than catching up with one of my childhood best friends when I’m home. Whenever we see each other, we always have so much to share—armed with notecards from our travels and little gifts that remind us of one another. The last time I saw her, she brought me a box of matches from her trip to London—something so uniquely me.

She’s always loved jewelry, ever since our days of playing dress-up together as five year olds. So, whenever I come across a beautiful piece, I immediately think of her. I’m so excited to see her when I’m back in December—she just got engaged, so I wanted to gift her a statement piece she can wear every day, as well as to any upcoming wedding events. The clover-inspired charm symbolizes luck, which is exactly what I’m wishing her as she begins this new chapter of her life.

Chunky U-Link Chain Necklace / Chunky U-Link Chain Bracelet / Freshwater Pearl Flower Charm

For Myself:

There’s nothing I love more than a classic jewelry stack—and this necklace-and-bracelet combination truly makes the outfit for me. The chain link is a favorite—it’s extremely chic on its own, but also feels playful dressed up or down with charms. I love that I can keep adding to it, too. Each charm can represent a moment in time or a special place in my life—like the martini olive for my time in New York, or the clover flower for a new beginning.

I’ve always loved olives (I order them almost everywhere I go), so the martini olive feels like a natural choice for my next charm, whether for the necklace or bracelet. There’s something so nostalgic about collecting charms; it’s what many of us did as kids, but I never really had the chance to do it in a more sophisticated way as an adult—until now. Playing with these charms has brought that back for me, and I can’t wait to continue adding to these pieces.

At one point or another in my life I have played soccer, basketball, volleyball and tennis, so it shouldn’t come as a surprise that a sporty sensibility has seeped into my everyday style. If I were to hazard a guess at why, it’s about performance. It’s not that I need to leave the house wearing some high-tech, sweat-wicking fabric or stride-optimized shoes; but rather, what I wear is designed in a way that gives me the tiniest advantage. I don’t like to use the word “optimized” because I’m not out here chasing perfection, but if a tee sits just so, or the shoes can handle my constant 10,000+ step days, that’s one less thing I have to think about.

That’s probably why my closet is stacked with the same prep-adjacent staples you’d find in the pages of Take Ivy. From the vintage tees I layer under blazers, to the track pants I throw on with a cashmere sweater, I’m always chasing a sort of transcendental bridging of the easy-dressy divide: put together without skewing too stiff or formal.

To prove my point, I handpicked five varsity pieces and styled looks that channel an effortlessly sporty energy—but thankfully leave the field (pitch, court, etc.) far, far behind.

Baseball Long-Sleeve Tee / Marled Cable-Knit Sweater / The Perfect Vintage Wide-Leg Jean in SoftDrape / O-Ring Studded Belt / The Idris Boot

1. The Baseball Tee

Having spent my formative teenage years in the midst of the early aughts baseball-tee trend, I still have a soft spot for these three-quarter sleeve, two-toned shirts. In fact, I like them so much that I don’t think they require much styling. Dressed up with a pair of boots, it toys with the inherent sportiness of the top.

Houndstooth Boxy Coat / Graphic Crewneck Tee / The Darted Barrel-Leg Jean / The Essential Belted Bucket Tote / The Mylie Ballet Flat

2. The Vintage Tee

When I interviewed for my first job, I showed up in a gray A-line dress and a pair of ballet flats—very boring, very professional and very not me. As soon as the interview wrapped (I got the job) my future boss said, “By the way, you definitely don’t need to dress so formally here; we all wear jeans.” So began my adventure in mastering the casual-cool work uniform. Whenever my look starts to feel a little too formal, I throw on a single sporty piece—like a vintage-inspired tee—to make it feel more true to my style.

CloudSoft Crewneck Sweater / Bootcut Track Pant / The Emilie Heeled Mule

3. The Track Pant

As a one-time sprinter who quit before making it to the varsity team, I think too many people overlook the versatility of track pants. They have the softness of a sweatpant, but with the structure and materiality that’s more in line with a trouser. That’s why I’ve styled them back to other pieces that share the same duality: a cashmere sweater that serves the function of a hoodie, and a pair of mules that slide on like slippers. It’s a lazy outfit (in the best way) that definitely doesn’t look it.

Polo Shirt in Stripe / Denim Trapeze Jacket / Flared Denim Midi Skirt, The Greta Lace-Up Ballet Flat

4. The Rugby Sweater

I’m a sucker for stripes, and this knit rugby top has that easy balance I’m always seeking. Sure, it’s athletic inspired (hence the rugby name), but the collar adds the same kind of polish I’d normally turn to a button-down for. For fall, I’m styling it with dark denim, which feels a little more seasonal than the light-wash styles I love in the summer.

Crewneck Varsity Sweatshirt / Slouchy Straight Pants / The Emilie Slingback Pump

5. The Sweater/Sweatshirt

There’s something satisfyingly cheeky about taking something as casual as a sweatshirt and styling it in a way that’s tomboyish yet chic—very Phoebe Philo coded. My approach: a streamlined color story, simple silhouettes and a sexy pair of shoes to balance out the sporty energy.

A Much-needed Reminder
Your perfect wardrobe should be—and is—vastly different from anyone else’s. This is a good thing. The beauty of this world comes from its variety and the unique experiences of its people, not from sameness or the influencer echo chamber—endlessly riffing off the same looks over and over again. It might sound cliché, but no one has your point of view. And that’s the way it should be.

Take, for example, a woman in her 70s I recently came across on Instagram. She’s dedicated her life to the color green—from the clothes in her closet to the shower curtain in her bathroom, it’s green everywhere. Chartreuse, evergreen, emerald, olive, sage. Why? From what I gathered, her reasoning is refreshingly simple: because she likes it. And who can argue with that?

How to Break the Cycle:

Study what makes you happy. Open your closet and become a student of yourself. This goes beyond clothes, to be fair. A fun activity? Pick out five pieces you can’t live without. What do they all have in common? Maybe it’s the craftsmanship of selvedge denim or the comfort of a well-worn tee. The key here is learning to differentiate between what makes you happy and what makes you happy that other people like it.

Clayton Chambers of Sprezza said it best:
“There’s a lesson in finding what you want when you stop trying. Just live your life. And your style will follow.”

No one can find “it” for you, though. The pieces that make you feel most like you. You have to find those yourself.

A Jumping-off Point:
Five essential pieces, five points of view. Which speaks to you?

1. The Cardigan
   You experience texture and softness on a different level. The warmth of a knit and romance of a cozy sweater feel like home.

2. The Polo
   You don’t overcomplicate things. Versatility is the name of the game. Throw it on, look like a million bucks. Simple.

3. The Jacket
   You live for the details. Down to the finishing stitches, you take everything into account. Looks are only part of it.

4. The Coat
   You’re inspired by vintage and the history of menswear. You admire the way your grandfather dressed and love to add a bit of polish to the everyday.

5. The Jean
   You recognize quality just by touch, appreciating that denim woven in Japan is as much a work of art as an oil painting.
   

Final Thoughts

Nothing is essential to everyone—especially when it comes to clothes. Sure, there are staple pieces like jeans, tees and the like, but those are just suggestions. Find what makes your wardrobe tick, and maybe you’ll find yourself in the process.

At Madewell, we believe in the value of well-made denim and the power of thoughtful design to extend a garment’s life beyond its first owner—that’s why we take denim back to be reworn or recycled through our denim trade-up program. Because whether it’s the clothes in our closets or furniture in our homes, the things that endure are often those built with a future in mind.

To explore what lasting design really looks like, we spoke to two vintage experts who embody this mindset: Jessica Li, owner of renewfinds in Greenpoint, and Kathleen Sorbara, owner of Sorbara’s in Williamsburg. Both have built businesses rooted in timeless design: Li specializes in carefully sourced vintage furniture, while Sorbara handpicks secondhand designer clothing—including an enviable archive of vintage denim. And while their domains may differ, their shared commitment to sourcing well-made items reveals just how connected these worlds really are.

First Life: Designed to Last

Think of a pair of jean’s “first life” as its first chapter—its time with the original owner. This stage matters because how a piece is designed, constructed and cared for early on determines what’s possible later. A well-crafted pair of denim has the potential to last far beyond its first wearer. As Sorbara puts it, “The pieces that stay in my closet the longest are things that last,” highlighting how timeless design and lasting quality are intertwined.

This philosophy also shapes how Li approaches furniture. Her focus on craftsmanship mirrors our approach to denim at Madewell: design isn’t just about style—it’s about longevity. “I pay close attention to construction—making sure it’s durable, sustainable and well made,” she says.

The same applies when choosing a new pair of jeans. Pay attention to the construction—seams, stitching, hardware—because these small details often reveal how well something is made and how long it will last.

Second Life: Denim Worth Passing On

Just because you’re done with an item doesn’t mean it’s reached the end of its life. When something is well made, it can be worn, loved and shared again. A pair of jeans begins its second life when it’s passed on—whether through our denim trade-up program, resale, repair, donation or simply being handed down.

This is where the character developed during its first life becomes even more meaningful. A secondhand pair of jeans might carry a story, but it still has room to grow in someone else’s wardrobe. Li sees this same dynamic in vintage furniture; the pieces she sources weren’t designed to be disposable—they were built to evolve.

To her, a well-earned patina tells an object’s story: “It’s similar to jeans—the rips, the tears, the fading. It’s lived in and imperfect, which makes it more special.” And whether it’s furniture or denim, that story deepens with use. From the crackled leather of an mid-century modern sofa to the faded whiskers on a well-worn pair of jeans, character comes from time, and time comes from quality.

Sorbara sees that same imperfect beauty in the vintage denim she curates: “It’s the little things that make items unique. You see washes with someone’s wallet imprint on the back pocket—you can’t replicate that.”

Ultimately, giving your jeans a second life is about recognizing that they still hold value, even if they’re no longer right for you. That’s why we created our denim trade-up program: to help you pass on what you no longer wear, so someone else can give it new life. As Li puts it, “Just because I no longer fit into a pair of jeans doesn’t mean they belong in a landfill. Being able to pass them on to someone who will love them as much as I did is beautiful.”

Third Life: Denim Transformed

Eventually, even the most loved jeans reach the end of their wearable life—that’s when their third life begins. Through our denim trade-up program, we’re able to take back jeans that can’t be resold and transform them into something entirely new.

So far, we’ve collected over 1.7 million denim pieces. Some are resold to be reloved, continuing their second life with a new owner. Others are transformed into something new through our partnership with Blue Jeans Go Green™, which recycles worn-out denim into insulation, sustainable packaging and more.

Letting go isn’t the end—it’s another chance for your jeans to do good. Ultimately, circular fashion doesn’t start at resale or recycling—it starts with the initial purchase. By choosing well-made, high-quality denim (or furniture) from the beginning, you’re not just shopping for today, you’re investing in pieces that hold up, evolve with you and live on in someone else’s closet long after you’re done with them.

At its core, style is circular—but only if it’s built to last.

• Andie MacDowell in The Object of Beauty: an oversized wool coat, undercut by a crisp white collar and red leather gloves.

• Isabelle Huppert in The Piano Teacher: rich charcoal layers, a pleated wool skirt, a pastel mohair cardigan.

• Linda Fiorentino in Jade: skirt suits, sheer tights and slingback heels.

• Emmanuelle Seigner in Bitter Moon: an undone trench, flashing thigh-highs (so many moments for sheer tights in the ‘90s).

• Juliette Binoche in Damage: black layers punctuated by a weighty silver chain necklace. Honestly, anything with ‘90s-era Binoche—Rendez-vous? Oof.

My wardrobe is inspired by my film watchlist, particularly European cinema from the late ‘80s through the early 2000s. Think foundational pieces and block colors—the “essentials,” if you will; pieces I’ve owned for years, some even passed down from my parents (like my mother’s camel cashmere round-collar coat or my father’s pastel-striped YSL dress shirt). There’s comfort in returning to clothes that have already proven themselves, but also in reimagining them, reshaping them and finding ways to make them feel new.

Oversized Button-Up Shirt / The Slouchy Straight Pant / Merino Wool Pullover Sweater / Sculptural Droplet Earrings / Contoured Statement Ring

That said, I’m not a morning person and I’m especially not a morning dresser. I need clothes that require no thought: easy enough to throw on for a 6AM call time, polished enough to carry me through a client dinner; pieces that are comfortable, versatile and still put together.

It might look like I’m wearing the same thing all the time, but one of my favorite Seinfeld scenes captures exactly how I feel about getting dressed. In it, Jerry asks George Costanza why he overpacked for a two-day trip when he basically wears the same thing every day. George responds by stating, “I happen to dress based on mood.” Jerry pushes back, “But you essentially wear the same thing all the time.” And George says, “Seemingly. But within that basic framework, there are many subtle variations, only discernible to an acute observer, that reflect the many moods, the many shades, the many sides of George Costanza.” Jerry asks, “And what mood is this?” Deadpan, George answers: “This is morning mist.”

Yes, my closet is mostly black, brown and navy—with the occasional deep red... and pleats (I love a Pleats Please!). But the nuances come through in the pieces themselves. A ribbed tee, for instance, is probably my most-worn item. Paired with a pencil skirt, it becomes my meeting look; styled with slouchy black slacks, it’s my shoot-day uniform; and for after-work hours, I’ll add a chunky silver chain (channeling Juliette Binoche, of course).

(Re)generative Cotton Cap-Sleeve Tee / The Slouchy Straight Pant / (Re)generative Cotton Elbow-Sleeve Tee

Another go-to of mine? A merino wool sweater—it’s functional, transitional and somehow makes even the simplest outfit feel intentional. It can be thrown on top or slung around my shoulders. The same goes for a crisp white shirt—collar peeking out from under a coat, dressed up with a skirt suit (à la Linda Fiorentino) or styled with a belted cardigan over structured denim.

Oversized Button-Up Shirt / Pointelle-Stitch Cardigan / The Balloon Jean / The Lexie Ankle Boot / Merino Wool Pullover Sweater / Single-Breasted Trench / The Deanna Thong Sandal

And then there’s the thong heel—peeking out from slouchy trousers or a pencil skirt—what my favorite fashion writer, Liana Satenstein (who got me into them in the first place), calls “a sickeningly sexy combination of filth and chaste.”

Single-Breasted Trench / (Re)generative Cotton Cap-Sleeve Tee / Oversized Button-Up Shirt / Milano-Knit Sweater Polo / The Slouchy Straight Pant / The Deanna Thong Sandal

These are the small shifts within my framework—the “morning mist” moods. A nod to the acute observer.

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This blazer from our fall collection has quickly become a favorite. The edit is full of staples you can dress up or down, mix and match and seamlessly pair with pieces you already own—like your favorite jeans or a cozy cardigan. I had some fun playing dress-up at the office and came up with three ways to style the blazer that feel perfect for easing back into a fall routine.

Look 1: Double Denim

At least once a week, I wear some iteration of the Canadian tuxedo. Accessories and third-piece layers are my secret to making it feel fresh—and tricking everyone into believing I’m not actually outfit repeating. Here, the blazer paired back to a statement brown belt elevates the casual base, while still keeping the look effortless and easy.

Cardigan Blazer | Tuckable Denim Shirt | The Dean Easy Straight Jean | The Essential Superwide Belt | Crystal Tennis Necklace

Look 2: Delicate Layering

This particular menswear-inspired print appears on several pieces throughout the collection, making it perfect for mixing and matching. One of my favorite ways to wear a matching suit is by layering it over something feminine and delicate to create a bit of tension. Here, I started with my go-to lace cami under a soft pointelle cardigan and finished the look with this blue wristlet for a pop of color.

Cardigan Blazer | Pointelle-Stitch Cardigan | Lace-Trim Tank | High-Rise Bootcut Trouser | The Sculpted Metal Wristlet | Wavy Chunky Ring | Dome Statement Ring

Look 3: The New Power Suit

I love how intentional and polished the blazer looks layered over the matching vest. To soften the look and keep it from feeling too serious, I paired it with white denim, which adds brightness and contrast—allowing the tailoring on top to really stand out. A studded belt and fringed suede bag round out the outfit for a fun, unexpected twist.

Cardigan Blazer | Crewneck Shell Vest | The Balloon Jean | The Essential Curve Medium Shoulder Bag | Studded Leather Western Belt | Two-Pack Mixed-Metal Cuff

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Sometimes, it’s the quietest things that stick with you: the way a pair of jeans fits without needing to be fussed with, the softness of a tee you’ve worn so often it remembers you.

When Madewell and Dakota set out to design two pieces, the intention was simple: something you’d wear again and again; a jean that feels like second skin; a tee that asks nothing of you and gives everything back.

What followed was the Dakota Longline Straight Jean and the Dakota Perfect Tee—two pieces born from detail, restraint and Dakota’s personal way of dressing: considered, clean, quietly confident.

The Beauty of Less

There’s something cinematic about Dakota’s presence—on screen, but also in a room. It’s not loud, it doesn’t demand attention, it just is. That energy guided everything: from fabric selection to fit to the cut of the tee’s neckline and the shape of the jean’s back pocket.

These weren’t designed to chase trends or create a moment. They were made to last beyond one. The Longline Straight Jean was adjusted repeatedly to hit at just the right point.

There’s a confidence that comes from wearing something that doesn’t ask for approval. That’s what Dakota wanted to capture. That’s what we hope you feel when you wear them.

Staples and North Stars

The Madewell x Dakota collaboration is only two pieces. They are perfect in their simplicity, designed to slip seamlessly into your wardrobe; they go together as naturally as they go with everything else you already wear.

The jean lives with you. Wear them:

• With your favorite vintage tee tucked in like an afterthought when you’re heading to the farmers market.

• With a French-tucked oversized button-up, looking effortlessly chic when you have to go into the office.

• With a silk cami, shrunken Lady Jacket and a kitten heel for an easy date night look.

• With an oversized blazer for a dinner out.

• Paired with a matching denim shirt for a double-denim moment.

• In the last days of summer, holding onto the warmth with strappy sandals and a flowy ruffled top.

• Transitioning into fall with matching boots and a belt.

• Straight into winter as the denim accent to your favorite overcoat.

• With the Dakota Tee, always.

The tee becomes you. Wear it:

• As the base layer under your favorite cardigan that you’ve worn for years.

• With slouchy overalls for weekend errands.

• Tucked into slim trousers with a heel to dress it up.

• Paired with a silk skirt, a study in textural contrast.

• With distressed denim shorts and a slingback flat that matches the stripes.

• With easy linen trousers for travel days.

• Under your favorite leather jacket.

• Beneath an open button-up for a light layered look.

• With the Dakota Jean, always.

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I couldn’t articulate it then, but I now understand that style has always gone deeper than just clothes for me. Like how an astrologer believes the planets shape our moods, I believe style shapes our sense of identity. Denim, in that regard, has always been the anchor. 

Do the jeans fit my style, or does my style fit the jeans? Denim reflects the way I hope to dress (and, by some extension, live). It’s cool but not aloof, structured but not stringent. It is the most adaptable of clothing items—equally at home in a dive bar or fine dining establishment. Denim is resilient too: spill something on it, rip it, scrunch it up, your jeans will still look good. In fact, with a little wear, they’ll look even better. 

For fall, I tried four denim fits from Madewell to see how they might help my style take shape this season. 

The Cleo 

The crisp, dark denim matches my energy immediately. Slung low on the hips (I sized up for a slouchier look), this pair strikes the right balance between casual and clean. That ease comes from both the fabric and fit—the Cleo has an old-school feel in 100% cotton with zero stretch. It feels reminiscent of my favorite vintage jeans, but reimagined in a straight cut that’s more modern and easier to wear. It’s a pair that could carry me through every iteration of my life. 

The Perfect Vintage Wide-Leg 

I’d guess the “perfect” in the name comes from its blend of structure and softness. When I first received them, I was surprised by their substantial, tactile thickness. On my body, however, these jeans feel limber and supple. I can wear them while sitting tucked into a ball at my desk (my preferred writing position) or through a full day of running around on set. Their wide cut lends a small girl like me a little extra attitude. I lean into the size, cuffing the hems and adding an oversized button-up. 

The Vintage Flare 

I’ll admit, this pair was the most intimidating on the hanger. Flares carry an unapologetic femininity, hugging my hips and emphasizing curves I might otherwise try to hide. But the nonstretch cotton gives this style a stiffness that makes me feel secure. The shape is subtle—a wink rather than an outright shout—and its flattering dark rinse wash suits my preference for sleek, minimal cool. Styled with a thick black belt and a white tee, I feel like Brooke Shields in the ’80s (minus a few inches, plus a few years). 

The Emmett Wide-Leg 

This is the lightest, most ethereal pair of the bunch. With their high rise and gentle shape through the hips, these jeans hold you without the squeeze; they have just the right amount of stretch. I could easily nap in them, but I wouldn’t want to hide this pair at home. A bright, light wash adds to their gossamer quality—though they certainly aren’t overly delicate. They’re the kind of jeans I’ll reach for on days when I want to capture an undone ease.

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Then something shifted.

It wasn’t just about durability anymore—it was about identity. Worn by rebels and icons, movie stars and musicians, denim became shorthand for cool. For ease. For authenticity. For effort that doesn’t look like effort.

And over time, denim didn’t just reflect culture—it helped shape it.

At Madewell, we never forgot where it came from. But we’ve spent years evolving to where it can go: signature fits, premium fabric, subtle details and silhouettes that support self-expression instead of dictating it. Because good denim isn’t just made well. It’s lived for. Loved hard. Worn in.

Dear Denim, let's get one thing straight about denim (flared, wide and ballooned): this isn’t just about you; it’s also about what happens next.

You don’t finish a look—you start it. You're the launchpad, the anchor, the quiet confidence under a loud coat or an airy tank. You’re the foundation that turns “I have nothing to wear” into “oh, wait—I do.”

And you’ve got range.

Let’s Talk Fits

The Balloon
You're artful, unexpected and a little exaggerated—in the best way. You don’t walk into a room; you float in, with volume, ease and just the right amount of “Is she cool or just confident?” (Spoiler: it’s both.)

The Cleo
Buttoned-up but never boring. You believe in patch pockets and big opinions. A little vintage, a little editorial and 100% that jean.

The Longline
Elegant without trying. You elongate everything—legs, lines, energy. They'll have to wear heels just to keep up.

The Pencil
Sharp, structured and secretly stretchy. You give office-core without the stress, and remind us that “flattering” doesn’t have to mean “tight.”

The Vintage Flare
You’re a time traveler with taste. You say “groovy” with one eyebrow raised. You make the sidewalk feel like a stage.

The Wide-Leg
Big energy, bigger hem. You’re roomy in all the right places—and leave room for thought, movement and whatever the day has planned (or not planned.)

Found your fit?
That’s when the real styling begins.

You start building the wardrobe, the look, the moodboard of who you are right now. These aren’t just jeans; they’re the beginning of your point of view. The through-line in your closet. The thing you reach for when everything else feels like a maybe.

The fit is Madewell. Everything after that? That’s all you.

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