Adidas Samba sneakers have moved beyond a mere trend to become a classic—a wardrobe staple that won't leave you looking dated. That said, maintaining that timeless appeal hinges on how you style them. While wearing Sambas with leggings and a sweatshirt is fine for a travel day, it misses the opportunity to create a cooler, more polished outfit. The chic approach for 2026 is to pair them with sweatpants and an oversize blazer.

Olivia Wilde is the latest stylish celebrity to showcase this outfit pairing. At CDG Airport in Paris, Wilde was spotted arriving for Paris Fashion Week wearing a casual yet elegant travel uniform: a black blazer, layered over a striped button-down top and a white T-shirt. On the bottom, she opted for black joggers and black Adidas Samba sneakers. She completed the look with her go-to Ray-Ban sunglasses, a tan leather tote, a black suitcase, and a leopard-print coat, which she slung over her luggage.

At Who What Wear, we often write about travel outfits and how to elevate your style while staying comfortable. After much research and covering some of these stories, I've concluded that when an elite traveler isn't wearing jeans, they opt for joggers, balancing the casualness of the sweats with a tasteful top and jacket. In this case, for Wilde, it's the relaxed blazer along with the button-down shirt, left undone and worn over a crisp tee, that's doing the heavy work. These pieces are a bit unexpected to be paired with sweats, which makes them look and feel interesting and unique. Plus, the layering is practical, since you never know whether the plane will be hot or cold.

Scroll on to see Wilde's recent look for yourself and shop Adidas Sambas—along with similar pants and blazers—to add to your 2026 wardrobe.

On Olivia Wilde: Adidas Samba Sneakers ($100)

Shop Adidas Samba Sneakers

Shop Oversize Blazers and Joggers

I used to avoid wearing sweatpants to the airport. I hate to say it, but I even secretly judged others for wearing them, considering the look sloppy and uncool. But more and more, I've noticed that people with good style have been wearing sweats, and there is a way to make them look polished. The key lies in selecting the right style of sweats and the shoes you pair them with. For instance, gray joggers paired with black loafers is a fail-proof pairing that looks very 2026 and elegant. One It girl who recently proved the look is supermodel Amelia Gray.

While stepping out before New York Fashion Week, Gray was spotted arriving at JFK Airport in a stylish travel ensemble. She wore a green winter bomber jacket paired with gray sweatpants. On her feet, she opted for black loafers and white socks to keep her ankles warm and protected from the chilly weather. For her accessories, she carried ALO's suede Tranquility Tote and a black suitcase, and she wore oversize sunglasses, which added a trendy touch.

On Amelia Gray: ALO Tranquility Tote ($2300)

Don't hesitate to pair joggers with loafers; just let me explain why it works. The key is the element of surprise. Remember the "wrong-shoe theory" coined by stylist Alliston Bornstein? Pairing loafers with sweatpants exemplifies it. While it may seem unconventional at first, deliberately breaking the norm makes the outfit feel very 2026, curated, and chic. Additionally, shiny black leather loafers instantly dress up the sweatpants, shifting the pants away from their casual vibe and adding a touch of elegance.

Next time you're traveling overnight across the country or leaving early in the morning for another destination within the U.S., and you want to wear sweatpants for comfort, consider Gray's example and pair them with expensive-looking loafers. Keep scrolling to get her look and see how I recently styled sweatpants and loafers for my flight from JFK to LAX.

How I Styled Loafers With Sweatpants for the Airport

Get the look: Suede blazer + zip-up sweater + gray sweatpants + black loafers

Get Gray's Look

Shop Sweatpants and Loafers

If Parke is already a permanent fixture in your off-duty rotation, this set of brands will feel instantly familiar. They sit squarely in that sweet spot between athleisure and everyday wardrobe staples, where comfort is a given but polish is nonnegotiable. Think crewnecks that hold their shape, sweatpants that look intentional with denim jackets, and loungewear that never reads like you're actually headed home. In 2026, this category isn't just about gym clothes—it's about a casual wardrobe that looks styled even when it's effortless.

What's especially notable is that the majority of these brands were founded by influencers who understood how women actually get dressed long before traditional labels did. These founders weren't designing fantasy fashion. They were creating the exact pieces they wanted to wear to Pilates, on flights, for school drop-off, and styled back to vintage jeans and sleek sunglasses. The result is a shared aesthetic language: elevated essentials, subtle logo moments, and silhouettes that feel modern without trying too hard. It's casual but considered, and that distinction matters more than ever.

The appeal is in the versatility. These are the pieces you throw on in the morning and never feel the need to change out of, whether you're running errands, grabbing coffee, or heading to a workout class. The logos are understated, the fabrics feel premium, and everything is designed to live comfortably outside the house. In 2026, this elevated athleisure space will continue to dominate because it aligns perfectly with how we dress now. It's less about outfits for specific moments and more about clothes that move seamlessly through your entire day.

If you love Parke, be sure to bookmark these seven brands as well.

Parke

Parke was founded by Chelsea Kramer as a response to how she—and so many women—actually wants to get dressed. The brand centers on strong, oversize staples that feel intentional rather than slouchy, from logo-forward crewnecks to relaxed sweatpants that hold their shape. What makes Parke stand out is its ability to straddle polish and ease, offering pieces that look just as good with vintage denim as they do worn straight out the door to Pilates. It's casual dressing with a point of view, and the pieces are designed to function as a modern uniform rather than just loungewear.

Brands Like Parke

Form

Founded by wellness influencer Sami Clarke, Form approaches activewear through a lifestyle lens rather than a trend-driven one. Its collections favor clean lines, neutral tones, and fabrics that feel supportive without looking overtly technical. The result is clothing that works quietly in the background—easy to wear, easy to style, and never shouting "gym." Form's appeal lies in its restraint, offering pieces that fit seamlessly into real life rather than dressing for a single moment.

Cotton Citizen

Cotton Citizen occupies a slightly different lane and was built on the idea that great basics should feel lived-in from day one. The Los Angeles–based label is best known for its signature washes and ultra-soft fabrics, which give even the simplest tees and hoodies a sense of character. These are pieces you build outfits around, not just throw on at home. As casual dressing continues to dominate in 2026, Cotton Citizen remains a go-to for elevated essentials that feel personal and timeless.

The Mayfair Group

Founded by Sam Abrahart, The Mayfair Group blends comfort with meaning in a way few loungewear brands manage to do. Its recognizable typography and message-driven designs turn familiar silhouettes into conversation pieces without sacrificing wearability. The brand's strength lies in its emotional connection. These are clothes that make people feel seen as much as they feel comfortable. In an era when community matters more than ever, Mayfair's pieces are designed to be worn out in the world, not just kept at home.

Anine Bing

Anine Bing has long defined what effortless dressing looks like. Built on founder Anine Bing's instinctive sense of cool, the brand isn't rooted in activewear, but its off-duty staples—soft knits, relaxed tees, and polished basics—naturally overlap with today's elevated, casual wardrobes. The mix of Scandinavian minimalism and subtle edge gives its pieces lasting appeal. In 2026, Anine Bing continues to anchor wardrobes with timeless essentials that make everything else feel more intentional.

Wiskii

Wiskii, founded by Katherine Tian, brings a distinctly refined sensibility to the activewear space. The brand leans into sculpted silhouettes and thoughtful design details that give traditional workout pieces an elevated, fashion-aware feel. There's a softness to the collections that makes them feel styled, not purely performance-driven. In 2026, Wiskii resonates with women who want their activewear to feel like a natural extension of the rest of their wardrobes.

Gold Hinge

Gold Hinge, founded by Katherine Watercutter, brings a playful, fashion-first perspective to sporty dressing. The brand draws inspiration from nostalgic athletic silhouettes while grounding them with modern proportions and easy styling. Its pieces feel intentional without being precious, designed to mix effortlessly with everyday staples already in your closet. In 2026, Gold Hinge feels especially relevant for those who want their casual wardrobe to feel current, relaxed, and quietly trend-aware.

Daily Drills

Founded by best friends Kennedy Crichlow and Mary Ralph Bradley, Daily Drills is built on the idea that getting dressed shouldn't feel complicated. The brand's relaxed sets, oversize crews, and cozy layers strike a balance between comfort and confidence and have an energy that feels approachable rather than overly styled. There's an ease to the collections that makes them ideal for travel, errands, and days that blur together. Daily Drills is embracing simplicity and making everyday dressing feel genuinely enjoyable.

Gen Z Says is a bimonthly column chronicling the latest trends in the fashion-and-beauty space through the lens of Who What Wear's own Gen Z editors. Expect a download on the upcoming class of tastemakers, emerging designers, and shopping and style choices straight from the generation setting the trends.

Gray sweatpants have quietly pulled off the biggest rebrand of the decade. Once the universal sign for “I’m not leaving my apartment,” they’re now doing double (and conflicting) duty as both the unofficial bed-rot uniform and the internet’s most classic 21st-century thirst trap. Twitter has litigated this extensively. TikTok has provided evidence. And Gen Z, naturally, decided to lean in.

You might not notice it at first glance, but slowly and surely, Gen Z is replacing their simple black leggings and barrel-leg jeans with gray sweats. Frankly, they've pulled off the biggest rebrand of the decade. What makes the gray-sweatpant comeback feel different this time is that it’s not about nostalgia or athleisure maximalism. It’s about contrast. The pants themselves are aggressively unremarkable—soft, slouchy, borderline boring. In my opinion, that’s exactly why they work. Instead of defaulting to chunky sneakers or hoodies, Gen Z girls are styling gray sweatpants with shoes that feel like they don't belong, embracing stylist Allison Bornstein's "wrong shoe theory," which fashion people relied on a few seasons back. Think sweats paired with designer ballet flats that skew sweet and coquette or kitten heels that suggest you might have a meeting later. Even full-on sparkly sandals are being paired with elastic waistbands like it’s no big deal.

This is wrong shoe theory in its purest form. Take something casual to the point of anonymity and throw off the balance. The Y2K crowd, of course, is doing their own version—gray sweats puddled over Ugg boots, channeling early 2000s mall culture and tabloid paparazzi pictures with a side of intentional irony.

The result feels effortless but very online, cozy but self-aware—like an outfit that knows it’s being perceived but doesn’t care too much. Gray sweatpants aren’t trying to be cool—Gen Z just decided they are (and styled them accordingly). Below, shop the best gray sweatpants and the off-kilter shoes that make them feel intentional, current, and winter-ready.

Shop the Trend

A few years ago, I never would've thought I'd be wearing sweatpant jeans, yet here we are. When they first launched, I heard all about them but was a bit hesitant. I learned to associate sweatpants with laziness, but when they look just like your favorite pair of wide-leg jeans, it's easy to be convinced.

After years of denim getting either more rigid or disappearing entirely in favor of trousers and knits, these soft, elastic-waist hybrids have quietly worked their way back into my consciousness, and honestly, I get it. Comfort is no longer a guilty pleasure; it's the baseline, especially for those of us who want to catch a red-eye flight overseas in both comfort and style.

This all being said, the 2026 version of sweatpant jeans looks nothing like the pairs we collectively retired years ago or the jeggings I'll never put my hands on again. The new styling is sharp, intentional, and surprisingly polished when done right. If you've been side-eyeing them but wondering how to wear them without feeling like you gave up, I've got you. These are the outfits that make sweatpant jeans feel fashion editor approved again.

This is the kind of outfit you throw on to run errands and somehow still feel chic—cozy layers, practical shoes, and sweatpant jeans that look polished enough to pass for real denim.

A classic striped sweater brings a French, off-duty ease that pairs perfectly with the relaxed silhouette of sweatpant jeans. Matching accessories pull everything together and make certain that they'll never know you're wearing sweatpants.

This is where sweatpant jeans really shine: travel days when comfort is nonnegotiable but you still want to look put-together. A denim shirt instantly sharpens the look and makes the whole outfit feel intentional, not accidental.

PS, I'm actually wearing these exact sweatpant jeans in this photo.

If you're worried sweatpant jeans skew too casual, I have a simple fix. A fur or faux-fur jacket adds instant glamour and proves these jeans can hold their own in a dressed-up moment.

When the base is simple, the accessories get to do the heavy lifting. A statement scarf adds personality and polish, making sweatpant jeans feel styled.

A strong coat can completely reframe sweatpant jeans, pushing them firmly into outfit territory. Think long, structured, or dramatic—this is where contrast does all the work.

Sometimes, the best approach is to lean all the way in. Treat them like actual sweatpants with a graphic tee, sneakers, and relaxed layers. Let the elevated cut and wash do the rest.

From mid-December through the end of the month, Aspen is the go-to place to be and be seen. All the coolest celebrities who live in L.A. leave the city and head to the snow. Whether they're there to ski, shop, or dine at Casa Tua, one thing is clear: They aim to demonstrate what Alpine-chic fashion means. Their standout looks often begin the moment they step off their private jets at Aspen airport. With the first set of A-listers arriving last week, many stars were spotted in cozy sweatpants paired with faux-fur coats, whether fully faux fur or with fur trim. Sara Sampaio and Shay Mitchell were prime examples of this stylish travel outfit formula.

Model and actress Sampaio was spotted wearing ivory sweatpants and a matching crewneck sweatshirt paired with a black fur jacket. For accessories, she chose a blue baseball cap, New Balance sneakers, and The Row's Margaux bag, a perfect travel bag for someone vacationing in Aspen.

On the other hand, the founder of Béis luggage, Mitchell, was seen wearing matching gray sweatpants and a crewneck sweatshirt, styled with a fur-trimmed leather jacket, black combat boots, a croc-effect Hermès Kelly bag, and, of course, her Béis carry-on luggage.

While sweatpants may initially seem like the ultimate "lazy" airplane outfit, think again. With the right styling, sweats can look tasteful. In fact, more and more elegant dressers are wearing elevated sweatpants outside of the home. Elsa Hosk is one of them. While she wasn't styling them for a travel day, she recently wore them in NYC with a matching sweatshirt, a long fur coat, pointed-toe heels, and an Hermès Kelly bag. Whether you're traveling this holiday season or just want to look stylish at home, follow the lead of Sampaio, Mitchell, and Hosk, and elevate your sweats with a faux-fur coat, an expensive-looking handbag, and sleek footwear.

Keep scrolling to see Mitchell's and Sampaio's Aspen travel outfits and shop the best sweatpants and faux-fur coats.

See the Aspen Outfits

On Shay Mitchell: Helsa Oversized Leather Bomber ($998); Béis The Carry-On Roller ($248)

Shop Sweatpants

Shop Faux-Fur Coats

A quintessentially L.A. stereotype when it comes to style is wearing sweatpants or yoga pants with Uggs. It’s been that way since the early 2000s, when iconic paparazzi photos of Paris Hilton and the Olsen twins in sweatpants and Uggs became a go-to.

Honestly, I was totally anti both as an adult—they reminded me too much of middle school—until this month, when I finally caved and picked up a pair of each to have on hand for winter errands and lounging at home. Every year around this time, I catch myself daydreaming about escaping the winter in New York and moving to L.A.: walking a dog I don’t have yet in yoga pants and Uggs, sunglasses on, enjoying the mild weather and sunshine.

Recently, Addison Rae and Lily-Rose Depp both wore this pant-and-shoe combination that’s making a comeback. With Black Friday and Cyber Monday sales still lingering, it’s the perfect time to shop the look. Ahead, a roundup of cozy pants and Uggs—many on sale for Black Friday and Cyber Monday—from Nordstrom, Gap, J.Crew, Aritzia, COS, J.Crew, Reformation, and more.

Shop Sweatpants & Yoga Pants

Shop Uggs

Sweatpants have a tendency to get a bad rep. They're called sloppy or too casual, while leggings are fine to be worn up and down, with blazers and kitten heels as well as sneakers and cropped puffers. Frankly, it's unfair, especially when sweatpants can look just as chic as leggings—that is, when they're styled the right way. The key is to pair your fresh and clean sweatpants and sweatsuits with hyper-elegant pieces that offset their comfortable, loose fit and soft fabric. Elsa Hosk, for instance, just wore a light heather-gray set with a long fur coat, an Hermès Birkin bag, and white pumps. Just like that, her cozy outfit transformed into an awe-worthy ensemble that she could wear practically anywhere.

Though her Birkin and heels certainly helped her case, the real reason Hosk's sweat set looks so elevated is her choice of coat style. Her floor-length, chocolate-brown faux-fur coat is from Helsa and, according to her Instagram post, it is now available to purchase (alongside her jogger set). The luxe material, which has long been associated with a rich, high-end lifestyle, was the perfect balancer, taking her sweats to a more formal, stylized level.

On Elsa Hosk: Helsa The Irina Faux Fur Coat ($649), The Full Sweatshirt ($198), and The Full Sweatpants ($229); Hermès bag

Get the Look

Hosk isn't the only one ushering this winter outfit into 2025, though. Across the pond in London, content creator Marilyn Nwawulor-Kazemaks is also wearing her gray sweats with fur coats, proving that this cold-weather uniform is global and ready for world domination. On Instagram, she posted photos of herself wearing ankle-fitted gray joggers with a fur-trimmed, waist-cinched coat and black slingback pumps, a somewhat unconventional outfit that somehow just works. It's warm and practical while still being high-end and cool.

All that's to say that while leggings can be a good pick for winter, before you rely on them all season long, give sweatpants another try. Just don't forget to style them with a fur coat to make them feel as 2025 as possible. Keep scrolling to find the best sweatpants and fur coats for your wardrobe this season.

Shop Sweats and Fur Coats

If you’re going to wear sweats this fall, there’s a right way to do it—and it has nothing to do with the oversize hoodies you wore to binge-watch shows last winter. The key to pulling them off in 2025 is all about proportion and polish. Think tailored silhouettes, sleek layers, and elevated accessories that transform your cozy set into something you could actually wear out. Sweatpants aren’t just for lazy Sundays anymore—they’ve officially graduated to the street-style big leagues.

Start by pairing your sweats with structured outerwear. A long camel coat or cropped leather jacket instantly gives off that effortless “I didn’t try too hard” energy. Add a fitted tank or crisp white tee underneath, then finish with a pointed-toe boot or retro sneaker. It’s the unexpected mix of soft and structured that makes the look feel intentional—and very fashionable. The goal is to look like you styled it on purpose, not like you’re running late for a flight.

Another foolproof way to wear them: tonal dressing. Matching your sweats to your top, coat, or bag in the same color family instantly reads elevated. Go all-grey with silver jewelry or try deep chocolate brown paired with suede boots. Keep the fit relaxed but not sloppy—cinched at the waist, slightly tapered at the ankle, and always clean. When your sweats look tailored, even a simple sweatshirt can feel put together.

Lastly, it’s all in the details. A sharp trench, chunky gold earrings, a structured tote, or even a sleek pulled-back ponytail can take your sweats from ultra casual to ultra chic. So yes, you can wear sweatpants this fall—but only if you wear them with structure, with tone, and with purpose. Because in 2025, cozy doesn’t mean careless—it means cool.

See the coolest ways to wear sweatpants this fall below and shop the essentials along the way.

Get the look: Long tan coat + faux fur-collar + grey sweatpants + pointed-toe heels

Get the look: Matching sweat set + ballet flats + mini purse

Get the look: Tank + loose sweatpants + dainty necklace

Get the look: Long jacket + turtleneck sweater + sweatpants + loafers

Get the look: Baseball hat + matching grey sweatsuit + sneakers

Get the look: Long coat + chunky sweater + grey sweatpants + suede loafers

Get the look: Crop top + matching sweatpants + brown suede bag + suede slides

Get the look: Loose cardigan + loose black sweatpants + flats

Get the look: Fitted tank + grey sweatpants + tall leather boots

Get the look: Collared sweater + matching sweatpants + suede ballet flats

Get the look: Lace top + sporty sweatpants + pointed-toe heels

Get the look: Zip-up sweatshirt + matching sweatpants + suede loafers

Get the look: Fitted long-sleeve shirt + oversize sweater + loose black sweatpants + black ballet flats

Get the look: Oversize hoodie + matching sweatpants + Uggs

Get the look: Black zip-up sweatshirt + white T-shirt + black sweatpants + sandals

When done right, a good collab can create fashion magic. It can tap into the cultural zeitgeist (Banana Republic x The White Lotus), generate international excitement (J.Crew x Rouje), and capitalize on celebrity appeal (Gap x Béis). The newest collab on my radar, Victoria's Secret Pink x LoveShackFancy, is well on its way to becoming fashion's most talked-about partnership.

The collection includes pajamas, ruched dresses, sweatpants, underwear, leggings, makeup bags, keychains, tote bags, T-shirts, and more. "The Pink x LoveShackFancy collection brings together the best of both brands—celebrating confidence-boosting style, friendship, fun, and, of course, our shared love of pink," said Ali Dillon, president at Victoria's Secret Pink. "We're excited to offer fan-favorite styles with LoveShackFancy's signature romantic twist and bring back nostalgic pieces from our archives. Designed to spark joy and real-life moments, this collection is perfect for taking you from high summer fun to back-to-campus style." Scroll down to shop my favorite pieces from the collab.

The Hamptons season has officially started. This means that by 2 p.m. every Friday, New Yorkers begin heading "out East"—to the land of Round Swamp Farm, vibrant hydrangeas, and $75 workout sessions. Leading the fashion scene is Mary-Kate Olsen.

This week, the Bridgehampton resident and co-founder of The Row was seen clutching a brown paper bag and an Amex black card on a grocery run. While Olsen, who’s built her career on her chic style, made the bodega bag look cool, it was her outfit that caught our eye: FreeCity sweatpants and flip-flops.

On Mary-Kate Olsen: FreeCity Sweatpants ($168); The Row sandals

On anyone else, this combination might seem like a relic from 2006. On Olsen, it was a master class in understated luxury combined with nostalgic normcore. She kept her usual loose silhouettes, pairing the sweats with an oversize tee. But the real detail? Those sweatpants weren’t just a random throwback; they were an intentional choice. FreeCity sweats are actually sold at The Row’s boutiques. In other words, these sweats are less of a “dated” item and more of a wardrobe staple that has the highest badge of honor—Olsen approval.

Then there were the flip-flops. Once confined to pool decks and pedicure chairs, the humble thong sandal has become summer’s most popular footwear trend. On Olsen, paired with loungewear and a nonchalant attitude, it created a look that whispered, "I summer in the Hamptons, but I couldn’t care less if you notice." Feeling inspired to replicate her stylish yet laid-back look this summer? Keep scrolling to shop the best FreeCity sweatpants and flip-flops.

If compliments are what you're after this spring (whether you're willing to outwardly admit it or not), a waisted cardigan has to be a part of your regular rotation—period. Unlike oversize and even super-fitted button-down knits, a waisted cardigan, with its hourglass shape and overall expensive-looking structure, is always the cornerstone of any outfit. Never will it play second fiddle to whatever skirt, jeans, or trousers you pair with it. It's consistently the breadwinner.

Because of its continued superiority in the sweater arena, I wouldn't judge you for investing significantly in a designer waisted cardigan. Hell, I've done it myself. But if spending $1000+ on a cashmere version isn't currently in the cards for you, don't fret. You don't, by any means, need to blow your budget—not when H&M has a $45 option that looks just as expensive as any hyper-luxury waisted cardigan.

H&M's new waisted cardigan options are available in colors like black and cream and feature a variety of details like tortoiseshell and gold buttons, cool necklines, and chic textures that only add to their rich appearance. Usually, pieces this good would have already sold out by the time someone called them out and brought attention to them. Fortunately for all of you, though, I check H&M on days when new items drop, allowing me to catch these finds early—so early, in fact, that they are still available in just about every size. I call that a modern miracle.

After you've snatched up one in each color, come back here and scroll through more compliment-worthy new H&M items for spring.

More H&M new arrivals to shop:

This post was published at an earlier date and has since been updated.

As we enter sweatpant season—which we can all agree is a thing—it's time to take stock of how we'll all be styling them this winter. Wearing sweatpants out in the world is a completely normal thing to do in our day and age, but there are ways you can go about making them look more polished and street-worthy. And Madelyn Cline just offered up one of them.

The actress was recently photographed wearing a pair of black ALO sweatpants with an item that instantly elevates the comfortable staple: an oversize blazer. Instead of an obvious choice such as a hoodie, Cline opted for a piece that added a bit more polish. And on this particular occasion, she completed the look with a baseball cap, black sneakers, and a Bottega Veneta Hop bag.

While there's been chatter lately of fitted blazers "replacing" oversize ones, I'm of the thinking that there's plenty of room for both styles to coexist in the fashion landscape, as they serve different purposes. And when it comes to which style to pair with sweatpants, oversize blazers take the cake.

Keep scrolling to see how Cline styled her sweats and shop chic oversize blazers to wear with yours.

On Madelyn Cline: Alo sweatpants; Bottega Veneta Large Hop Bag ($4900)

Shop Oversize Blazers to Wear With Sweatpants

The most apt description of Daily Drills and the brand's overnight fame can be boiled down to a video link we sent to the team's publicist with the message "Oh my god??" In it, a band of 20-somethings documents their journey of waking up at 4 a.m. and waiting in line in anticipation of Daily Drills' pop-up at La La Land Kind Cafe in Dallas, Texas, along with at least 60 other young women who were up before dawn and hoping to snag a sweatshirt. Although co-founders Kennedy Crichlow and Mary Ralph Lawson couldn't have imagined it when they first started the line in 2020, it's now become the norm for the beloved internet brand.

Enter Daily Drills, one of the direct-to-consumer activewear and loungewear brands to pop up during the pandemic. Unlike many of them, though, Daily Drills is still massively successful beyond the era of whipped coffee and dyed sweatshirts. Crichlow, Lawson, and their devoted fan base have shed their sweat suits in favor of a chicer, more elevated take on a lifestyle and resort brand. There have been pop-ups in New York and Dallas, and judging by the brand's online success, there are plenty more to come. Plus, the drop-based model that inevitably sells out leads to customers wanting more and more.

"We believe there is room for every lifestyle brand when you stay true to yourself," Lawson and Crichlow tell Who What Wear. "Sure, there are plenty of lifestyle brands out there, but there is only one of us."

It's hard to miss. We've in the midst of a sweat suit boom for a while, with every celebrity, influencer, and cool girl attempting to make their online audience convert into monetary sales, but there's something different about the women behind Daily Drills. They're both fashion-industry and social-marketing vets with a self-funded mission that feels more akin to entrepreneurship than an opportunity to capitalize off of a TikTok algorithm. Frankly, they know it too: "As long as we focus on our own styles versus just chasing the next trend that the rest of the fashion industry is following, there's space for us all."

You two were friends long before you began the brand—we'd love to hear the story of how you two first met and what pain points you had that led you to start Daily Drills.

We first met while contributing to a shared fashion IG account. Each girl who was a part of the account posted on a different day of the week. When we finally met IRL while we were both in L.A. for college (Ken at Loyola Marymount and Ralph at Pepperdine), we became fast friends.

We were feeling uninspired by our careers and closets, so when the world shut down during the pandemic, we had a chance to reflect on our lives and decided to take the leap and start Daily Drills. Everyone strongly encouraged us not to mix business and friendship, but we both have different strengths and interests, which make us work so well as a team. We have definitely found our groove. It's been one of the great joys in our lives!

Daily Drills has such a large, dedicated fan base. What does engaging with your audience mean to you, and how do your customers inform your drops? Have you figured out why they keep on coming back?

Our customers mean everything to us because they are our community! Although we haven't fully cracked the code yet and are always looking for new ways to engage with them, we are so grateful and honored by their dedication and are constantly inspired by their comments on our social media. We're in our DMs every day chatting with them in real time, and we love that they are never afraid to tell us what they want. We like to keep the line of communication as open as possible so that we are truly bringing our audience in—whether that be through in-person pop-ups, community events, online master classes, or sorority chats. We want there to be an open-door policy.

We also travel to the places our customers love to vacation and want to vacation in and share behind-the-scenes content and travel guides along the way. For example, everyone who vacations in Aspen was super excited to shop the recent Aspen collection because it feels personal to them!

We'd love to hear more about the business model in approaching your collections like limited-edition, one-time drops. What was the decision going into that? Do you think that's led to the buzz around the brand?

We didn't anticipate being a drop-based business! On the first drop, we couldn't afford a large amount of inventory, and when it sold out, we were shocked. We immediately reinvested the profits into more inventory, and then that sold out again. Naturally, that created a pretty high demand, and the buzz just spiraled from there. We're constantly trying to keep up with the demand, but so far, it's been so fun releasing collections with new designs and themes biweekly so that our customer always has something fresh to look forward to!

There are so many lifestyle, resortwear, and loungewear brands hoping to get a piece of the pie. Especially since the pandemic, DTC cozywear brands have exploded and become a big part of the fashion conversation. Where do you see the industry evolving from here in a post-pandemic world?

One of the only good things that has come out of the pandemic is making loungewear socially acceptable! Comfort has always been key when it comes to fashion, but now, it's a priority, and we don't think that's going anywhere. We love finding ways to style our sweats up and have enjoyed expanding into resortwear that's a bit more elevated but still just as comfy.

People will only get more creative and more bold from here. The oversize look has really expanded from lounge to ready-to-wear—e.g., blazers, loose trousers, button-downs. We've even been seeing it in top-tier designers recently, like Miu Miu, who are leaning into the sporty-chic side of loungewear.

As female entrepreneurs, what advice would you give to your younger selves or other female founders who want to start their own companies and brands?

Starting is the hardest, most intimidating part! If we can do it, so can you! Don't be worried if your first product isn't your best. It's not supposed to be. Just keep ideating and working toward the bigger vision.

Princess Diana Style

One of our go-tos is the Oversized Crew with bikers, socks, and loafers or chunky sneakers for chic, sporty on-the-go look.

Matching Sweat Set

You also cannot go wrong with a matching sweat set to elevate your airport look for style and comfort.

Sweater, Shorts, and Boots

We recently have loved styling our Single Button Sweater with long shorts and boots (like Ken did for the opening of the NYC Daily Drills pop-up) or with the Poplin Resort Pants for a more laid-back look.

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It recently came to my attention that the term casual isn't in my vocabulary. According to one of my closest friends, I haven't dressed casually for a day in over twenty years. Sure, I've been backpacking but I did so with floral accessories in my tresses, my day tote was a matching patent number and my High School bag of choice was a mini Adidas backpack complete with pink stripes, whilst most of my peers donned Nike's more practical iteration. Whilst admitting defeat and pondering over this (fair) observation, I started to envisage the ways I could welcome casual pieces into the fold, the Avalon way.

Despite what it may seem, I'm not averse to casual clothing. 2023 was the year I embraced the sweatshirt as a piece to disrupt my knitwear collection, appreciating it as a pared-back alternative to fuzzy knits. It's true that it's a considered transitional piece that sits in-between a t-shirt and the higher wool content of a knit. Last year, I even acquired a cap for the very first time and it's been a game-changer for morning jaunts. There does come a time (long winter walks, errand days and hikes, for example) where a dress will (sadly) not suffice.

I've always admired pared-back styling and off-duty looks (Princess Diana being one of my muses during her era of nonchalant dressing), however, I've come to realise that I'm more comfortable in frocks and skirts. It's my version of dopamine dressing. With this in mind, and the use of innovative styling, I've found a way to marry elements of casual and formal. For fellow "overdressers", you've come to the right place as I've created five inspired outfits comprising a sweatshirt, for your foray into casual dressing. You can't say I'm not trying!

5 Chic Sweatshirt Outfits For Spring 2024

1. Melange Sweatshirt + Cargo Pants + Pointed Ankle Boots

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2. Sweatshirt + Full Denim Skirt + Mesh Ballet Flats

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3. Black Sweatshirt + Leather Jacket + Column Maxi Skirt + Trainers

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4. Brown Sweatshirt + Crew Neck T-shirt + Boyfriend Jeans

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5. Knitted Sweatshirt + Burgundy Bag + Leather Trousers

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Next Up: People in London and Paris Are Swapping Their Ballet Flats for This Sleek Shoe 

Just tell me you wouldn't get an instant confidence boost wearing cashmere. It's that kind of mood-boosting inner confidence you get when you are wearing a favorite new piece or special underwear or that feeling after getting a new haircut and blowout. This hilarious and iconic TikTok about cashmere and The Row also helps set the scene. That exact vibe is all I needed to motivate me to find the chicest cashmere pieces online right now.

I know, I know—cashmere is notoriously pricey, but there are some more affordable pieces available this season. (Thank you, fashion gods!) Plus, at the end of the day, any investment you make on a cashmere piece will guarantee a major ROI since you will wear the hell out of each piece for many years to come.

Keep scrolling to check out the top five cashmere pieces to keep an eye out for this season along with a chic selection to shop and elevated outfit ideas to get you inspired. From cardigans to dresses to sweaters to pants, there is something for every personal style.

Fitted Cashmere Cardigans

Fitted cashmere cardigans are having a major comeback this season. The minimal '90s-inspired style is super sleek and comes in a variety of colors and cuts.

Cashmere Pants

Cashmere is already so luxurious, but cashmere pants are next-level luxe. What's great is that they are perfect for lounging and running errands and can even be dressed up with polished shoes and sleek outerwear in today's casual-chic climate.

Cashmere Sweaters

There's nothing more timeless and versatile than a cashmere sweater. You can wear them for any occasion, in any color, and with everything from jeans to skirts to even dresses.

Oversize Cashmere Cardigans

Oversize cardigans are a favorite among the fashion set. Make it cashmere and it's the ultimate piece for cooler weather. These are great for wearing alone or layered over a variety of looks.

Cashmere Dresses

Sweaterdresses make for easy dressing that doesn't sacrifice style. The one-and-done piece is even more elevated when it's made of cashmere. Thankfully, there is a stylish pick no matter your preferred dress length and sleeve style.

If you were privy to conversations in my inner circle as of late, you'd likely have gotten an earful of my and my husband's avid interest in moving to Europe. Current political climate aside, the fashion, especially in Amsterdam and Scandinavian capitals like Copenhagen, Oslo, and Stockholm, is another major reason I am yearning to head abroad.

There are six aspects that encompass the particular European style that I love and admire. Thanks to the hyper-connected fashion world we live in, it's not rare to see these stateside in places like NYC and Los Angeles, but it just doesn't compare to the real deal. Whether it's button-downs, cool dresses, comfy yet chic flat shoes, or standout accessories, there is just something about the whimsical and cool approach to styling outfits I can't get enough of. Keep scrolling for some great outfit inspiration and plenty of European-inspired fashion picks for getting the look.

1. Unexpected Use of Color

There is something about an unexpected pop or mix of colors that brings me so much joy. It could be a bright bag or shoes added to a minimal and monochrome outfit or a cool color combo (like Sidsel's above) that always leaves me wondering why I hadn't thought of that mix.

2. Stylish Flat Shoes

One thing is undeniable when it comes to style in Amsterdam, Copenhagen, and the like—stylish flat shoes reign supreme. Whether it's ballet flats, chunky booties, sneakers, strappy sandals, loafers, or clogs, these comfortable shoe styles are the go-to, no matter the occasion.

3. Sporty-Chic Details

I am the queen of comfort, so I am not mad at the fact that there is a whole community of fashion people that consider sporty pieces as chic, elevated options for everyday looks. And this was all before the pandemic amped up everyone's athleisure game to the max.

4. Comfortable Yet Luxe Staples

There's an ease that Europeans, especially Scandinavians, have when styling luxe staples like button-downs, linen pants, sweaters, silk dresses, etc. The ensembles always look comfortable yet polished with a touch of whimsy.

5. Cool Dresses

Cool dresses and European It girls go hand in hand in my book. Whether it's a simple dress or one in a vibrant color or standout print, they are bound to be painfully cool.

6. Playful Bags and Accessories

If you haven't caught on by now, I am a huge fan of outfits that have a fun, playful vibe. Europeans stylishly (and confidently) pull this off with the help of a whimsical bag or accessories like ruffled ankle socks and a quirky hat.

Next: This Flat-Shoe Trend Is Growing Among Fashion People, and It's Great With Jeans

Are sweatpants the new leggings? The new jeans? When it comes to post-pandemic dressing, casual pieces are more acceptably integrated into everyday looks. Combining your comfort clothing with your elevated staples makes for the ideal hybrid wardrobe. And yes, it can still look chic.

The art of combining these pieces is relaxed, effortless styling, which admittedly can be less effortless than it seems. Oversize blazers, longline coats, and luxe handbags are a few of the key pieces to execute this perfect mix. 

This may be one of those trends that you may see others in and think looks aspirational, however, when it comes to re-creating, it’s trickier than it looks. So I’ve pulled inspiration from some of my choice influencers for some outfit ideas that will be seen at my local coffee shop. And, of course, I’ve shopped out a few pieces you might need to get the look.

Oversize Blazer + Sneakers

In my opinion, a boxy blazer equals instant elevation of any look. Tossing it over a matching sweat set is an unexpected way to dress up your comfies. Top the ensemble off with a coordinating baseball cap and sneakers.

Shearling Coat + Socks + Loafers

Ultra-cool styling is this shearling-trim coat with the sock and loafer combination. Put a quirky printed sweater underneath and, of course, a luxury bag to take it to the next level.

Hat + Long Coat + Pumps

Pumps with sweatpants are a major Rihanna vibe. Matching the accessories color-wise is the key to executing on this outfit.

Cable-Knit Cardigan + Shoulder Bag

For an on-the-go look, pair your coziest cardigan with a pair of sweatpants and sneakers. And don’t forget an accent shoulder bag.

Bomber Jacket + Sneakers

A black sweat suit is a sure bet for elevating your sweats. Throw a leather bomber jacket over it for a whole look.

Next: It's True—Everyone Is Wearing This Shoe Style With Leggings Again

Sometimes, even Jennifer Lopez needs to just throw on some simple sweatpants, boots, and a sweater and go on a coffee date. The superstar was spotted with her new husband, Ben Affleck, in Santa Monica grabbing a venti Frappuccino. Perhaps a little whipped cream is a trick she's trying to lure the longtime Dunkin' Donuts devotee over to Starbucks? Either way, we're taking notes.

But seriously, if Lopez wears sweatpants to grab a morning coffee, then the laid-back look is fair game for everyone else, too, no matter where you choose to quench a caffeine craving. Unlike J.Lo, however, we'll be saving the Valentino sweater and Brunello Cucinelli hiking boots for our afternoon coffee break. 

Ahead, shop sweatpants, sweaters, and boots that are stylish enough for a daily coffee run. The only decision left is whether make it a grande or a venti.

Re-Create J.Lo's Coffee-Date Look

Next, J.Lo Just Wore the $69 Bra That's Absolutely My Next Lingerie Purchase

As I live in New York City, it can be hard to relax. Whether it be the battle of bodies rushing in and out of the subway, the constant honking and sirens swarming the streets, or the nagging feeling that there's always something else to do, New Yorkers rarely can enjoy a minute of calm. While there are a plethora of options to aid in relaxation—Thai massages, waterfront walking paths, happy-hour steals—none of these are sustainable for everyday life. 

And then, I discovered a solution. It came to me one day when I was working from home. I was lounging in sweats on my couch with my computer open, and I could not focus. So I went to my closet, pulled on a pair of black jeans and a blouse, and sat back down. Immediate focused, I spent the rest of the afternoon more productive than I'd ever been. "Dress for success" may not be a new concept, but "dress for relaxation" is. Now I'm not saying to forgo all structured items of clothing and move about in balloon pants, but wearing more relaxed clothing is a sure way to put your mind and body at ease. Pairing straight-leg leather pants with a simple tank or an easy cardigan with slouchy jeans is truly the definition of ultimate relaxation. And New York has never felt so peaceful. Keep scrolling for the easiest items to perfect your new relaxed style.

Up next, I Didn't Think I Needed New Shoes—Then I Saw These Trendy Styles at Nordstrom

Although Jennifer Lopez is often dressed to the nines (she does have plenty of occasions to dress up for, after all), she's also no stranger to a good loungewear look. Whether she opts for leggings, track pants, a matching set or sweatpants, Lopez always looks completely put-together and stylish. This time, it was a jogger look that she mastered.

There's nothing new about people wearing sweatpants outside the house, especially over the past couple of years. We thought we'd covered every possible jogger outfit trend imaginable, but J.Lo just found another one, and it's particularly fresh for 2022. The reason? She paired an oversize bomber jacket—from & Other Stories, no less—with her grey baggy sweats and Nike Air Jordans. You probably remember that bomber jackets were absolutely everywhere at one time, but did you know they're a thing again? Only this time around, it's oversized bombers that are making the trend feel fresh.

Read on to shop Lopez's comfortable, stylish sweats look for yourself, and shop oversized bomber jackets to wear with your own joggers (because we all have them).

On Jennifer Lopez: & Other Stories Bomber Jacket (£120); Nike Air Jordan Sneakers (£115)

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This story originally appeared on Who What Wear U.S.

Next Up: Jennifer Aniston and J.Lo Both Wore the Denim Trend I'm Replacing Skinnies With

Although Jennifer Lopez is often dressed to the nines (she does have plenty of occasions to dress up for, after all), she's also no stranger to a good loungewear look. Whether she opts for leggings, track pants, a matching set, or sweatpants, Lopez always looks completely put-together and stylish. This time, it was a sweatpants look that she mastered.

There's nothing new about people wearing sweatpants outside the house, especially over the past couple of years. We thought we'd covered every possible sweatpants outfit trend imaginable, but J.Lo just found another one, and it's particularly fresh for 2022. The reason? She paired an oversize bomber jacket with her grey baggy sweats and Nike Air Jordans. You probably remember that bomber jackets were absolutely everywhere at one time, but did you know they're a thing again? Only this time around, it's oversize bombers that are making the trend feel fresh.

Read on to shop Lopez's comfortable, stylish sweats look for yourself, and shop oversize bomber jackets to wear with your own sweatpants.

On Jennifer Lopez: & Other Stories Bomber Jacket ($149); Joah Brown Oversized Joggers ($148); Nike Air Jordan Sneakers ($195)

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Next up, see how Kim Kardashian styled the new version of the bomber jacket.

There are only a few experiences I greatly relish—that first sip of iced coffee and finding an incredible secondhand designer piece included. But lately, the only thing I can think about (besides finding affordable holiday gifts) is the prospect of lounging around at home in lingerie for the rest of the year. I dream of silk slip dresses, lace teddies, and bouclé robes that I can snuggle up in, crack open a coffee table book, and disappear from the internet for the rest of the holiday season. Does the idea of lounging around have you daydreaming about your days off ahead too? Then you’ll want to keep reading, as I’ve rounded up the coziest lingerie to spend the rest of 2021 in. Say goodbye to sequins and hello to silks. 

Cozy Lingerie Under $50

Cozy Lingerie Under $150

Cozy Lingerie to Invest In

Next up, Weird—the "Sexiest" Lingerie I Own Is Actually the Most Comfortable

I really don't like cold weather. For someone who is from Chicago, stayed on the East Coast for school, and now lives in New York City, I really didn’t plan that very well. Even as I write this, my hands are terribly dry, my lips are chapped, and my hair is all staticky. The heat in my apartment is too hot, but without it, I’m too cold, and so the list of winter woes goes on. Yet despite my disdain for frigid temperatures, there is still one reason keeping me in it: winter clothes.

Seriously, I love cold-weather clothing. Chunky scarves, puffer bombers, fuzzy socks—something about it all really appeals to me. I love curling up on our couch in a head-to-toe sherpa ensemble feeling like I’m entering my own hibernation den. There’s no better feeling than ultimate coziness, which you just can’t get in any other season. I mean, maybe I’m slightly obsessed with sherpa and my favorite animals are polar bears, but cozy hibernation seems to suit me.

So in order to mentally prepare for the winter, I scoured the internet looking for the best cold-weather clothing on the market. This year, I hit the jackpot. After searching across a variety of websites, I found myself spending the most time scrolling through Amazon’s endless options of quality winter clothing. To save you the hours of searching, I rounded up all of the cute cold-weather finds hiding on Amazon below.

Despite all my winter qualms, I really can’t see myself moving anywhere without all four seasons anytime soon. As much as I love a good beach vacation or long summer nights, without the cold weather, I would not appreciate the warmer months as much. So I think I’ll stay in New York for a little while longer.

Plus, what would I do with all of my cute cold-weather clothing? 

Up next, We Found 30 Fun Tops, Dresses, and "Leather" Jackets, All Under $50 (Seriously)

It’s snowing, and it’s time for spring cleaning. Yes, I know it’s still winter, but my New York shoebox apartment is bursting at the seams with clothing, and I need to condense. 

See, I am what some would call a hoarder. I love all my clothing and have such a hard time getting rid of pieces. This may be one of the reasons I have a beanstalk of a shoe rack stacked on top of my closet filled with pairs of shoes I have not touched in five seasons. It took going home for Thanksgiving and coming back to really look at my room with clear eyes and come to see that this is no way to live. And thus, spring cleaning commenced before the holidays. 

Throughout my cleaning process, I realized that the most important things are the basics. While I have glittery sneakers and funky, furry coats, I really only wear my closet staples: my favorite jeans, classic black leggings, a white tank top, and other solid pieces that make up my day-to-day wardrobe. And as much as I love an occasional pop of color or texture, it’s time to make room for my closet’s basics because those are the clothes that I actually live in.

The best part about these closet basics is that they can go with literally anything and be worn any which way. A simple leather jacket can drape over something as casual as a denim dress or be thrown over something as classy as a black LBD. And so I moved all of these staples to the front of my closet and moved my, say, less conventional pieces under my bed. 

Now when I go to my closet to pull an outfit together, I see all of the basics I know I actually wear, and I can think of at least 15 ways to wear these useful closet basics. I’ve rounded up some of my favorite staples below.

Up next, I Ordered 3 Cozy Amazon Basics - Here's My Unfiltered Review

I am sick of being uncomfortable. My day-to-day outfits are always so structured. Whether it be skin-tight leather pants to work, a bodycon dress on a night out, or even just mid-rise jeans to go run errands, my body is being constantly squeezed by fabric and sometimes I just want to let everything loose.

I had just gotten home from a day at the office, when my roommate burst in through the front door. She said a quick hello to me and our dog and then made a beeline for her room. She emerged after no more than twenty seconds, no longer in what I call her "paralegal power pantsuit” and instead in a cozy purple sweatsuit. 

"Where in the world did you get that?” I said, immediately envious of her cozy attire.

"Amazon,” She said, and immediately I grabbed my computer.

There was the solution. Comfy clothing, cute enough to wear outside or inside, that won’t break the bank. I scrolled through endless options of cute, cozy clothes that I couldn’t wait to change into the second I came home from work, a wild bar night, or a day out and about. 

Fast forward 24 hours to my roommate and I lounging on our couch in matching sweatsuits, with our dog longingly gazing at our outfits (or our fried rice, not sure which).

Keep scrolling for my 24 clothing picks from Amazon that are comfy and stylish.

Up next, A Little List of Every Fall Wardrobe Essential in My Shopping Cart

Gigi Hadid has worn many great airport outfits over the years, and the main takeaway is always that they're relatable. She keeps things casual and practical for flights, just like most people do. Sneakers, leggings, oversize outerwear, and T-shirts are a few of the basics she always incorporates into her travel outfits, and we love to see it. For her latest flight (across the pond to Italy for Milan Fashion Week), Hadid reminded us that sweatpants can be very cool, which you may have put out of your mind since it's been 90ºF for months.

Hadid opted for a pair of white sweatpants with a T-shirt, shacket (trend alert!), bucket hat, and fun Converse high-tops. She looked fresh, comfortable, and stylish, and we can't wait to re-create the look ourselves for our next flight (even if it isn't to Italy). Scroll on to find out how to do that, and shop some of the best sweatpants we've seen so far this fall.

On Gigi Hadid: Free People FP One Scout Jacket ($128); The Row N/S Park Leather Tote ($2750); Converse Chuck 70 Hi Sneakers ($94); Le Specs Outta Love Sunglasses in Sangria ($59)

On Gigi Hadid: The Row N/S Park Leather Tote ($2750); Converse Chuck 70 Hi Sneakers ($94); Rimowa Essential Cabin Suitcase in Mango ($720)

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