Your early 20s can be such a confusing time. This is the time a lot of people are not only entering the professional workforce but also discovering their style. As a fashion editor, I find joy in helping people find pieces they love at an affordable price point, so I decided to use my expertise to help my 23-year-old younger sister. I utilized my knowledge of top-tier internet hot spots and voraciously dug through many a virtual aisle to uncover some pretty cool pieces. 

Ahead shop my Gen Z style picks that any early 20s fashion lover will be excited to check out. From comfortable, trendy sneakers and cool tops to beautiful accessories and chic cold-weather finds, there's a diverse array of product selections to cater to a range of tastes. Keep scrolling to find your new favorite styles.

All the Ways to Wear is a monthly series where we round up the personal twists the Who What Wear team is putting on one particular item, style, or trend. Whether it’s the trending denim of the moment or the season’s It print, we hope to inspire your daily outfits and up the cost per wear on some of our favorite items.

In this month's edition of All the Ways to Wear, we're excited to be spotlighting our very own designs that just launched. That's right—we've collaborated with fashion girl–favorite footwear brand Sperry for the second year in a row. This year, we're back with not one but two new shoe styles. What can we say? We love to give the people what they want. First up is a leather mule (offered in both black and ivory) with luxe faux-fur lining and contrast stitching. The second is a sleek white sneaker with cream suede details. Both of our latest footwear designs are perfect for all of your fall outfits, and to prove it, here are eight of the best looks we've seen styled with the new shoes (so far anyway).

"This outfit is a great go-to for pre-fall. A pair of your favorite jeans with a staple white T-shirt is what a classic look is made of. The mules help keep this look casual and fun, and they're great to throw on for a casual day of errands or shopping." — Stephanie Leigh, content creator

"It's the year of the flat shoe, and I'm really leaning into it with this super-chic mule. Get ready for your new go-to of the season. Right now, I'm wearing it with maxi skirts and tanks, but come cooler weather, I'll be swapping those out for cozy sweaters and trousers. Not only is the cute mule easy to walk in, but it's incredibly cozy. Yes, there is actual faux fur lining the inside to keep your toes nice and snuggly for the winter months. And the contrasting white stitching on the black leather is *chef's kiss.*" — Anneliese Dominguez, senior editor

"These mules spoke to me. I love how comfortable they are, yet they look almost like you're wearing boots. My inspo behind this outfit was to feel on-trend while still looking professional. I would wear them with dresses, jeans, skirts—basically everything." — Kim Pardo, content creator

"I've been a big fan of mules for a few years now, but I've never owned a flat pair like these. The leather is so lovely, and I especially love how comfortable they are, too. I'm so into maxi skirts and vests right now, so naturally, I styled the mules with these pieces for a casual look that's still elevated. I'm looking forward to pairing the shoes with fun socks and cool trousers as the temperatures dip." — Chichi Offor, associate shopping editor

"The sneakers are great for walking around the city or grabbing brunch. I styled the sneakers based off wanting to be comfortable but also look chic and put-together. The black midi dress with the black belt is providing the chic element whereas the sneakers are providing an element of comfort and coolness to the look." — Leigh

"The ratio of sneakers to all the other shoes in my closet is getting bigger by the minute. I can never have too many pairs of sneakers. Whenever there's a comfortable shoe that can also be stylish, count me in. White sneakers are my favorite of all time, so you know I was immediately drawn to this pair. You can really style the shoe with anything and everything: super-casual jeans and tees or more elevated dresses and skirts. There's no wrong answer. The retro style is right on par with what every fashion girl is roaming the streets in this year." — Dominguez

"These are the perfect sneakers that go with everything from jeans to dresses. It’s all about comfort, and I love that I was able to pair these with a dress to go from work to dinner with the girls." — Pardo

"I'm all about a go-with-everything closet piece, and these sneakers are just that. The simple yet stylish design makes them perfect to style with a wide range of looks. You can never go wrong with a crisp button-down and jeans. These Sperry sneakers were the perfect addition and matched seamlessly with the easy, no-brainer outfit. I can see myself wearing these shoes with everything from simple dresses to chunky sweaters." — Offor

With so many friends sharing stories about airlines losing their luggage, I've become a firm believer in the carry-on suitcase. Last summer, I managed to pack for a two-week vacation (for two very different cities, might I add!) in one small bag, and I've been on a roll ever since. But that means I have to be very particular about what comes with me. I'm always on the hunt for pieces that can be worn multiple ways because I'll likely have to repeat a few throughout the trip. (Sue me.) So I was super excited to hear from three fashionable frequent fliers (who you likely already follow on IG) that Sperry shoes were on their list of must-pack items this summer for this very reason. And after seeing how they styled them, I'm more than ready to throw any of the below pairs in my suitcase for my next getaway. Curious to see what I mean? Keep scrolling.

Paloma Meehan, Content Creator

"These shoes are perfect for vacation since they're neutral and go with the majority of my closet! Sperry shoes are so cute and easy to wear with any minidress, maxi skirt, or your favorite pair of jeans. They have a classic and timeless style that has remained popular for decades, so they're always in fashion and can be worn year after year without looking outdated (which is truly why they're my favorite). Did I mention that they're seriously comfortable? Whether you need a casual shoe for everyday wear or a dressier shoe for a special event, these shoes should be your go-to."

Meghan Adams, Digital Creator

"I brought these Sperry shoes along for my European vacation this year, and I couldn't be happier. After getting married in Tulum, my husband and I never took a honeymoon, so we're counting this trip as one! Sperry's boat shoes are not only comfortable but also practical, making them the perfect choice for this trip. They're versatile and can be worn with a wide range of outfits whether you're out for a stroll on the beach or dining out in the evening."

Taryn Cumbo, Content Creator

"Summer 2023 is all about being adventurous, and Sperry is the epitome of adventure while staying comfortable and looking cute at the same time. What could be better? You could say I'm a bit obsessed with the brand. I've worn the shoes all my life, and they truly never go out of style. This year, I'll be styling my Sperry shoes with high socks—I think the look is so cute and adds an extra layer of comfortability, making them the perfect addition to my summer vacation wardrobe."

Shop More Vacation-Worthy Sperry Shoes

When it comes to summer shoes, Georgie Morley (the photographer you've definitely seen sharing her East Coast style all over TikTok) is certain she's found the perfect pair. And what might those be, you're wondering? A pair of platform Sperry sneakers inspired by the classic boat shoe. "I love crisp, white shoes for summer," the Nantucket native tells me. "They instantly give you that on-the-water feeling when you put them on. And the classic white just adds to the versatility. They're sleek enough to dress up or down." I'm someone who likes to invest in one pair of shoes to wear with basically everything in my closet (not to mention I'm an avid lover of neutrals), so naturally, I'm intrigued. Luckily for me, Morley is sharing three ways she's styling these shoes below. And between the ecru pants, pretty dresses, and breezy linen tops, these looks are more than ready to be packed on your next getaway (or worn on a warm summer weekend at home). Ready to see what she put together? Keep scrolling, and start making room in your closet for a new pair of shoes.

SHOP THE SHOES

"I wanted to create a neutral, monochrome-ish outfit, so I paired the ecru wide-leg pants with a tan sweater and white platform sneakers.These boat shoe–inspired sneakers and surfboard sweater both create a subtle ocean aesthetic that gives this outfit an unmistakably summer feeling. I'm already planning on wearing this look while watching the sunset on the beach with friends and a bottle of wine." — Morley

"This look screams coastal grandmother. I was inspired by where I live in New England. The style is so timeless and quintessentially summer. It gets chilly here on Nantucket, even in the summer, so you always need layers like blouses and sweaters. Truthfully, this is my go-to out-and-about outfit—you can wear it anywhere. It's so easy to wear and remix over and over. And the shoes play up that classic, heritage New England feeling." — Morley

"I wanted to mix the shoes with a dress and loved the casual, flowy factor of this purple-checked dress. I love the combination of sneakers with a dress. It feels so fun and youthful! I'd wear this for a casual date night or lunch with my friends. The look is comfortable enough to be active in, too. It's so fun to make a dress a little more casual with sneakers. The white canvas and platform also bring a modern, youthful edge to the outfit." — Morley

SHOP MORE SPERRY SHOES

The coast is calling, and it's only right that I answer with booked flights and packed bags. But with so many destinations ahead of me, where do I even begin? No trip to a coastal town is complete without a pair of timeless Sperry shoes, and the brand's latest offerings are the reinvented classics I've been looking for. Every style from the Authentic Original™ Boat Shoe to the new SeaCycled™ Platform Sneaker is inspiring and elevating my vacation looks. There's nothing worse than looking back at photos and completely cringing at the outfits I put together, but these five are really hitting the mark if I do say so myself. So if you're headed to one of these destinations or looking for a dose of vacation outfit inspiration, keep scrolling to shop the looks I'm taking with me.

When packing for Montauk, go for elevated beach essentials. Swap denim shorts for a cotton pair, a baseball cap for a structured bucket hat, and a beach tote for a mini bag. But the number-one must-have for a trip to the East Coast beach town is a pair of Sperry boat shoes. I adore this navy-and-white combo for any coastal vacation, but they feel especially perfect for the Hamptons aesthetic.

When it comes to packing for a trip to Miami, you need pieces that will take you from the water to the beach club. We've got the bikini set, cover-up dress, a pop of color in the accessories, and the easiest slip-on Sperry sneaker. This outfit will have you feeling put-together even when you're coming straight from the sand.

To go from brunch to the boat on a Charleston vacation, this is the outfit to pack. A floral maxi dress, a sweater to throw over your shoulders, chic accessories, and the Sperry Authentic Original™ Boat Shoe are really all you need. This look encompasses that classic Southern charm while bringing in on-trend elements.

A trip to Malibu is all about relaxation, and your outfit should be just as laid-back. Opting for a one-piece swimsuit, staple denim shorts, and trusty beach hat is the way to go. Finishing off with a simple, baby-blue crossbody and platform Sperry shoes adds a bit of fun to a simple beach-day look. This is a no-fuss outfit that still maintains a level of trendiness.

Hawaii is the epicenter of corny tourist outfits, but this one is anything but. We've got a tasteful floral handbag, a modern-day shell necklace, and a pair of fun sunglasses that match the rich botanical color of the islands. Coordinating with this neutral Staud dress and Sperry boat shoes makes for the ultimate fashion-person take on vacationwear.

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No one knows how to dress for winter like an East Coaster. New Jersey–based content creator Allison Whalen is no exception. Her Instagram feed offers a master class in everyday layering, featuring an endless array of luxe sweaters, laid-back flannel, artfully draped scarves, and cozy footwear. "Living in New Jersey, it can definitely get really cold, but I try to make an effort to get outside everyday,” she tells us. "Having warm footwear makes a huge difference in my morning routine.”

Her go-to shoes for surviving even the coldest days of the season without going into hibernation mode are Sperry boots. They’re incredibly comfortable, cozy, and can tackle any terrain, snow included. Read on to see how she’s expertly styling them this season.

"Sperry’s Plushwave 3D Boots are the perfect pick for a winter hike,” Whalen explains of her first look. "They’re so comfortable while still keeping my feet warm! I styled them with an all-black look and a bright-pink beanie for a pop of color!”

"I absolutely love the faux-fur accents on Sperry’s Torrent Lace Up Boots,” Whalen exclaims. "I styled them in a casual, everyday outfit I’d typically wear with snow boots. I think a sweater and leggings with a cute pair of snow boots is the most perfect winter OOTD!”

"I styled these sherpa-lined duck boots for a rainy day spent running errands,” she says of her last look. "I love how the blue in my jacket complements the gray boots!” (We’ll also award bonus points for the well-coordinated umbrella addition.)

SHOP MORE SPERRY BOOTS

When it comes to boots, I'll try just about any trend or style at least once. Between chunky Chelsea boots, lace-ups and quilted rain boots, I've yet to meet a style I don't like. Because I'm in the mood to pretty much exclusively wear boots right now and because the rainy, snowy (even muddy!) weather often requires them, I've styled five looks around my new favourite pairs from Sperry. No matter what type of weather I'm dressing for on any given day, I can rely on this brand for stylish footwear that will take on the elements. If you're ready to switch up your go-to cold-weather outfit or simply craving some fresh boot-styling inspo, you're in the right place.

No matter the season, I'm always going to gravitate towards black-and-white outfits. There are few color combos as chic, in my opinion. For this reason, I'm loving these black Sperry Chelsea boots with the chunky black sole. Plus, the rubber material means I can stomp through puddles and mud without ruining my shoes. I kept the majority of the apparel black with white details to keep things feeling elevated and to coordinate with the boots. Did I nail it, or did I nail it?

For an outfit that's a bit more elevated, I'm loving these heeled duck boots. They add a bit of polish to the outfit while still being perfect for a rainy day or night. I kept the rest of the outfit pretty neutral with an ivory sweaterdress, a plaid scarf and tan, leather accessories. Even if the forecast shows sunshine, I'd still wear this cute and cosy look.

I know everyone loves a good denim-and-boots outfit, and I aim to please. I wanted to keep things interesting, though, so instead of classic brown boots, I opted for this two-tone pair (which just so happens to be water-resistant, by the way). I like the idea of styling these with knits in a similar colour palette and then balancing it all out with polished, wide-leg jeans and a sleek shoulder bag for a look that feels casual yet sophisticated. The beanie is optional, but I'll be grateful to have it when it starts to snow.

These boots are ideal for when you need to wear weather-friendly footwear but don't want the look of traditional rain boots. The fact that these have an on-trend lug sole and are a slip-on style sold me. For a sporty vibe, I styled the boots with elastic-waist cargo pants, an oversized knit and a bag and zip-up jacket both made of nylon (because it's not just the boots that need to withstand the rain). Catch me in some version of this look—if not this exact one—on the weekends until further notice.

Duck boots are my go-to for rainy days, but this leather pair is next-level cool. I had to style them with a sherpa bucket hat and other cosy pieces like a knit dress and wool socks. Just don't forget an umbrella.

When it comes to boots, I'll try just about any trend or style at least once. Between chunky Chelsea boots, lace-ups, and quilted rain boots, I've yet to meet a style I don't like. Because I'm in the mood to pretty much exclusively wear boots right now and because the rainy, snowy (even muddy!) weather often requires them, I've styled five looks around my new favorite pairs from Sperry. No matter what type of weather I'm dressing for on any given day, I can rely on this brand for stylish footwear that will take on the elements. If you're ready to switch up your go-to cold-weather outfit or simply craving some fresh boot-styling inspo, you're in the right place.

The website description of these boots claims they're "like a mattress for your feet," and I have no further questions. It's not only the comfort that sold me but also the easy slip-on style that makes this pair feel almost like sneakers. I leaned into the sporty vibe of the footwear with this outfit, styling the boots with elastic-waist cargo pants, an oversize knit, and a bag and zip-up jacket both made of nylon (because it's not just the boots that need to withstand the rain). Catch me in some version of this look—if not this exact one—on the weekends until further notice.

I know everyone loves a good denim-and-boots outfit, and I aim to please. I wanted to keep things interesting, though, so instead of classic black or brown boots, I opted for this two-tone purple pair (which just so happens to be water-resistant, by the way). I like the idea of styling these with knits in a similar color palette and then balancing it all out with polished wide-leg jeans and a sleek shoulder bag for a look that feels casual yet sophisticated. The beanie is optional, but I'll be grateful to have it when it starts to snow.

Duck boots are my go-to for rainy days, but this sherpa pair is next-level cool. I had to style them with a bucket hat in the same texture and other cozy pieces like a knit dress and wool socks. Just don't forget an umbrella.

No matter the season, I'm always going to gravitate toward black-and-white outfits. There are few color combos as chic, in my opinion. For this reason, I'm loving these white Sperry Chelsea boots that have a chunky black sole. Plus, the rubber material means I can stomp through puddles and mud without ruining my white shoes. I kept the majority of the apparel black with white details to keep things feeling elevated and to coordinate with the boots. Did I nail it, or did I nail it?

If you thought those purple boots were fun, then may I interest you in this baby-blue pair? To really give these quilted duck boots the moment they deserve, I kept the rest of the outfit pretty neutral with an ivory sweaterdress, a plaid scarf, and tan, leather accessories. Even if the forecast shows sunshine, I'd still wear this cute and cozy look.

Welcome to our podcast, Who What Wear With Hillary Kerr. Think of it as your direct line to the designers, stylists, beauty experts, editors, and tastemakers who are shaping the fashion-and-beauty world. Subscribe to Who What Wear With Hillary Kerr on Apple Podcasts and Spotify.

Who What Wear's editor in chief, Kat Collings, had the European adventure that dreams are made of. If fashion week—really fashion month—wasn't enough going on, Collings had her wedding in the South of France along with an epic Italian honeymoon.

During her trip to Europe, Collings was able to get a firsthand look at what locals on the streets of London and Paris are wearing this fall. Don't worry: Comfort is still in, guys. "The comfort thing is real coming out of the pandemic. It's cool because you look really stylish and current too," Collings says.

If you've been looking for the perfect boots for fall and winter that can withstand the wintery elements, Collings shares a behind-the-scenes look at what it was like to design the Sperry x Who What Wear Duck Float Boots, which are available now. If you're planning a fall wedding, Collings has all your packing and styling needs covered, too, as she breaks down how she managed to pack for fashion week, her wedding, and her honeymoon. 

In the latest episode of Who What Wear With Hillary Kerr, Collings shares how the trends differ across the major European fashion capitals, how she packed for her trip, and so much more.

For excerpts from the interview, scroll below.

You are officially back just in time for fall and just in time for the debut of a very fun fall collaboration that we did at Who What Wear with the one and only Sperry. You worked really hard to bring this together. Can you bring us inside the details of the Duck Float Boot and what it was like bringing this project together?

It is a very special boot. I am obsessed with it. I'm so proud to have this released out in the universe. I think this boot is really the perfect blend of function and fashion. It has this waterproof duck shell on the bottom with these traction pods.

The shaft of the boot has contrast stitching. It's premium leather, it's sleek, it has subtle moto vibes, so it feels current but also very classic. You could wear it for many, many seasons to come. It's relatively lightweight, so it's easy to wear. I got to have the privilege of modeling some of them, so I've wear-tested them, and they're really, really comfortable. I think [it's] really just the perfect fall-to-winter, bad-weather-season boot.

You had all of these wedding festivities, and I would imagine that you had your outfits quite planned out for that. Can you talk me through some of your favorite looks, how you styled them, and your wedding dress?

For my wedding dress, I wore custom Danielle Frankel. [The brand is] really the fashion girl's bridal outfitter of choice in my opinion. I actually tried on the dress that I ended up getting—or a version of it—in February 2020 at New York Fashion Week, so I've had the dress sitting in my apartment. It was so exciting to finally wear it and have people react to it. I had been sitting on it for so long, so it felt fresh all over again, which was amazing. It was really fun to work with Danielle [Hirsch] on the dress and with Christy Baird of LOHO Bride, who was the L.A. counterpart to all of this.

How did you think through all of your looks?

I just thought of my events and the location. We were in Nice on the beach in the South of France as well as where we did the welcome beach day. The rest of the events were near St. Paul de Vence. When I was thinking about my rehearsal dinner, I was like, "You know, I could go for something loud and bridal." But I went with this Totême bustier that I've since worn a couple times and some white jeans. I was so excited for the beach day to find this crochet dress that was inspired by this one that Jane Birkin wore. It felt appropriate for the setting, too.

For my second look, I got to wear a design by Anna October, this Ukrainian designer. It was from her resort 2023 collection. She made this collection—she had to flee Ukraine—and made it in Paris. The design community there really helped her out. Celine donated the fabrics, and another brand donated the space for her to work in. It's this patchwork dress that has these amazing gloves that go with it. [It's] made from what fabrics were available, so that was kind of cool to be able to wear something with a bit of meaning behind it for that second look.

Tell me a little bit about what you saw in terms of key pieces, styles, trends, and what people are wearing in Europe at the moment.

In terms of the average person out there who's looking stylish, a lot of the more Gen Z people I noticed were wearing some sort of stretch flare—the "not quite pants, not quite leggings" situation that the Emma Chamberlain crew has been promoting. It makes a lot of sense. They're quite flattering and comfortable and just easy to wear. Then with sneakers… so many sneakers. Really, the sneaker du jour is the Adidas Samba. The comfort thing is real coming out of the pandemic. It's cool because you look really stylish and current too.

In London, what's always interesting is—it sounds stereotypical—you really do get the sense that there's always a little bit of a perverse punk edge there. It's so signature to London and special and unique about that city. Paris is always the most polished, classic. It's a bit more traditional. You want to add that extra dose of sleekness. Whether it's a big, structured blazer that you're wearing with a sheer little pencil skirt. If you're going to wear heels, it's definitely the place to wear heels. It's the most dressed up. You see a lot of that on the fashion circuit, but then for the real-life Paris stuff, again, that was where I saw so many sneakers. You see a lot of individuality too. I do think it categorically has the best vintage scene as well. 

This interview has been edited and condensed for clarity. Next up, check out our previous episode featuring Kendra Scott.

It may sound counterintuitive, but there are few things in life that yield more pure joy than a good old-fashioned rainy day. There’s the rhythmic pitter-patter of droplets hitting the roof overhead, the adrenaline rush that comes with trying to make it inside without an umbrella, and the fresh, earthy smell that follows a torrential downpour.

Of course, to make the most of a rainy day, it’s important to ensure you’ve got a few fashion essentials ready to go. For advice on doing just that, we turned to TikTok, where there’s never a shortage of fashion inspo. Take a look at the four next-level rain-boot outfits that fashionable content creators dreamed up around their go-to Sperry styles, and you’ll be ready the next time your local weather forecast shows storm clouds on the horizon.

Here on the West Coast, we take any excuse to bring out our seasonal staples. "I wish we got more fall weather in L.A., but as soon as the weather dips below 70º, I love to put on a cute outfit and go for a walk to get a coffee,” says TikTok influencer Ella Miller. Exhibit A: this comfy layered look that consists of a crisp white jumper, baggy cargo pants, and fleece-lined Sperry rain boots. "Rain boots aren’t always super comfy, but these were so easy to enjoy my long walks in, and they still look cute!” she adds of her go-to pair.

"As soon as it’s cool enough, I can’t wait to get my boots out for the season,” says Hannah Hartvigsen, a Chicago-based content creator whose TikTok feed is brimming with bursts of plant life and pops of color. "They’re the perfect finishing touch to any fall outfit and make facing colder weather a breeze.” Her rain boots of choice? Sperry’s Duck Float Zip boots, which she’s expertly paired with her quilted floral jacket to brighten up the gloomy weather.

"I’ve been seeing a lot more color this fall, and that excites me!” says content creator Marie Zoumanigui of Petite Marie NYC. "Just because it’s gloomy outside doesn’t mean your style has to feel gloomy.” Here, she put together a look that’s anything but. "Cute and comfy was my mindset,” she explains. "It’s still early fall, so I wanted to show off some leg with the skirt while making sure my feet were dry and warm. My Sperry duck boots came in handy and made this look perfect for a rainy day.”

Who says rainy-day looks have to feel dreary? Certainly not New York–based TikTok influencer Victoria Casalino, who paired her favorite rain boots from our Who What Wear collab with a miniskirt, a cozy sweater, and a puffer jacket. "Boots are a must-have in my fall wardrobe because they match everything and always make me look more put-together—especially my Sperrys!” she says of this casual-cool, rainy-day look.

SHOP MORE SPERRY BOOTS

Boots are an absolute cornerstone of any fall wardrobe, so when we got the opportunity to team up with Sperry on a footwear collaboration, I knew it was the first type of shoe I wanted to tackle. After a year of sketches, samples, and swatches, I’m so pleased to share our first release: the Sperry x Who What Wear Duck Float Boots. I may be a bit biased, but I don’t think there are better boots out there for the season ahead.

What’s to love about these boots? Let me count the ways. They are the perfect blend of style and service. The contrast topstitching and sleek ankle shaft are trend-forward yet classic. The lightweight, waterproof shell is ideal for tackling inclement weather while still looking put together. And at the price of $130 for real leather shoes? Well, that’s a sellout risk, folks. Ahead, I’m sharing a sneak peek into the design process and outfit ideas straight from me and our stylish editors. But first, make sure to secure your pair of Who What Wear-approved boots just below.

SHOP THE BOOTS

THE DESIGN PROCESS

After we decided to kick off our partnership with a pair of boots, we went straight to the Sperry archive and current catalog for inspiration. I have memories of my stylish mother wearing Sperry duck boots growing up, so I was immediately drawn to the idea of incorporating the waterproof shell into the design. Sperry’s Duck Float style caught my eye, and I thought the more rugged, practical base would be the perfect partner to a sleek leather "city-boot style” shaft. I aimed for a study in compatible contrasts, as I find some of the best design moments balance two different aesthetics for a nuanced, visually interesting effect.

Then it was on to the details! I love contrast stitching because it lends a bit of edge and highlights the lines of a design. An embossed logo on the heel became our subtle branding moment, and we went for classic color choices of black and a rich caramel brown to ensure you get the most wear out of your investment. On a practical note, the rubber sole has traction pods to help stay upright in slippery weather. Overall, the boots are a chic blend of form and function.

OUTFIT IDEAS

In addition to a smashing pair of boots, an oversize blazer is a fall must. Add a miniskirt plus a turtleneck, and your look will be equal parts on-trend and classic.

I’d make a bet your closet has all the items needed to re-create this effortless look. Leggings are perfect to show off your new boots, and a crisp Oxford shirt and casual sweater over your shoulders add polish. 

I love a look that throws fashion rules to the wind. Long shorts plus mid-calf boots may seem intimidating, but this outfit is proof the proportions can work, especially when paired with a sophisticated tank.

If the long-shorts look isn’t your speed, the outfit also works well with a pair that hits mid-thigh. For one of those early fall, warmer rainy days, a bucket hat is the perfect complement to your waterproof boots.

When the colder temps hit, all you need is a cozy sweater set and your all-weather boots. I love how the hem of the midi skirt just grazes the top of the boots, so both pieces get their moment to shine.

Still warm where you live? Check out how to style Sperry’s classic boat shoe.

All the Ways to Wear is a monthly series where we round up the personal twists the Who What Wear team is putting on one particular item, style, or trend. Whether it’s the trending denim of the moment or the season’s It print, we hope to inspire your daily outfits and up the cost per wear on some of our favorite items.

It's that time of year when I take inventory of my current wardrobe before shopping for new seasonal pieces. And when it comes to my shoe collection, I'm pretty set on boots. I have dozens of pairs that range in style: heeled, lug-sole, cowboy, combat, Chelsea, sock boots, and so, so many more are sitting in my closet as we speak. I was all but convinced I wouldn't want to add more boots to my lineup this season, but apparently, I was wrong. (Oops.)

As soon as I saw the first sketches of the boot that our Who What Wear team designed with Sperry, I knew I would have to break my "no new boots" rule. This duck boot comes in two colors and features all of the on-trend details you'd expect a team of fashion editors to select, including a chunky sole, a cool zipper, and exposed stitching. And of course, it has the durability and comfortability that only a heritage footwear brand like Sperry can pull off. I had to make a little extra room for them in my closet, and I'm so glad I did. See how my fellow editors and I are styling the Sperry x Who What Wear boots as we start to dress for fall.

"During the fall, I'm a boots girl through and through. I'm always on the hunt for new styles to add to my collection, so you can guess how excited I was to try this new Sperry x Who What Wear collaboration. These boots aren't only chic (can we take a moment for the white stitching?) but practical as well. Gone are the days of ruining a pair of shoes in unpredictable weather—I know these will hold up no matter what. Plus, the black color is so easy to style. You can dress them up with a cool midi dress or keep them more casual like I did here with some leather shorts and a knit vest. Either way, you're bound to get compliments." — Anneliese Dominguez, editor

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"I'm really into the contrast between the gorgeous brown leather and the black EVA base (which, by the way, is waterproof) on these boots. It feels very cool and modern while maintaining the look of a traditional duck boot. My favorite way to style them is with any type of pant that can be tucked into the shaft (think skinny jeans or faux-leather leggings) and an oversize top or sweater. It's the perfect everyday fall look, rain or shine." — Michaela Bushkin, associate fashion director

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"I can't pretend that I'm even remotely happy about summer ending, but fall in NYC is like no other, so I'm prepared to dress accordingly. These boots are my new go-tos. The rubber and leather hybrid with the white contrast stitching is a unique twist on the classic black duck boot. I kept this outfit super neutral and edgy, leaning into the punk aesthetic that's been trending lately. I'd wear this to a casual dinner with friends or even a concert since these boots are so comfortable and easy to walk in." — Aniyah Morinia, associate editor

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Some pieces never go out of style, and Sperry's iconic boat shoe is one of them. Lately, they've really been having a moment with the fashion set here in NYC. I've been spotting them all over town styled up with summer staples like floral minidresses or dressed down with classic denim cutoffs and ribbed tanks. They're a stylish staple that can be worn with practically every outfit in your closet. Over the years, Sperry has expanded its boat shoe selection, and it has enough variations and playful colorways to go with any outfit I currently want to wear. In short, I'm convinced these are the most versatile shoes on the market. To prove my theory, I created five looks for every summer activity. Going on a boat trip? I got you. Grabbing brunch with girlfriends? There's an outfit for that. Keep scrolling to see the shoppable looks I created with the shoe of the season, all of which will keep you stylish all summer long. You're going to want to see these.

Whether or not you're going boating, this is summer 2022's quintessential outfit. You have a matching linen set, '90s-inspired sunnies, a raffia chain purse, and of course, leather boat shoes to match.

For me, weekends are all about outfits that are both put-together and casual. I love a one-item outfit with elevated accessories to get me out the door, metallic Sperrys included. 

What more could you need for a day at the beach? It's all right here: swimwear, trendy denim, stylish sun protection, a large tote, and shoes you can slip on and off with ease. This pastel pair with perforated detail feels extra beach-appropriate. 

I spend 90% of my hot summer weekends picnicking in NYC parks, and I've perfected the ideal look: breezy trousers, cotton tanks, fun accessories, and the ultimate Sperry boat shoes, which pack major dad-style energy.

This outfit will keep you looking stylish on and off the court. All you need is a preppy dress that's still breathable, a sporty dad cap, a trendy shoulder bag on standby, and classic preppy footwear to swap for your tennis shoes post-lesson.

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All the Ways to Wear is a monthly series where we round up the personal twists the Who What Wear team is putting on one particular item, style, or trend. Whether it's the trending denim of the moment or the season's It print, we hope to inspire your daily outfits and up the cost per wear on some of our favorite items.

I can still remember my first pair of Sperrys. I begged my mom to get them for me for Christmas even though I lived in Northern California, where the cold temps called for footwear more along the lines of wellies and fur-lined boots (whoops). Still, I think I ended up wearing them almost every day that year. Fast-forward to today, and the preppy trend is making quite the resurgence in the fashion scene. And of course, the style set is hopping on the wave quickly with pieces like pleated miniskirts, polo shirts, and—yep, you guessed it—Sperry boat shoes. I tapped two of my editor friends, Michaela Bushkin and Sierra Mayhew, and one incredibly stylish TikToker, Dannaed Garcia, to see how they're incorporating the shoe style into their wardrobe rotations this spring. And trust me—you'll want to take notes. Keep scrolling to see all the ways to wear Sperry's most iconic shoe.

Dannaed Garcia, Content Creator

"I'm so happy that preppy style is in this spring. When I was a kid, teenagers dressed preppy, but I was too young to dress up. I'm super excited to experiment with my style this season. I'll for sure be incorporating modern preppy pieces like Sperrys into my wardrobe. Not only are they classic, neutral shoes, but I love how comfortable they are. (And when I say comfortable, I mean I can literally run a mile in them and not feel a thing.) They go with any spring look, including dresses, skirts, shorts, jeans, and even athleisurewear. They are just so versatile and so classy."

Michaela Bushkin, Senior Fashion Editor, Who What Wear

"I'm a denim girl all year round, so I'm happy that my Sperrys looked so cute (if I do say so myself) with this wide-leg, light-wash style I'm loving at the moment. The navy shoes and blue denim work together from a color perspective, so that's where I started. I wanted to incorporate another bright hue that would complement the navy footwear, and I landed on this green tank top and sweater (because even in L.A., weather can be unpredictable). I like the juxtaposition of the blue and green shades here. It feels so fresh for the spring season."

Sierra Mayhew, Associate Editor, Who What Wear

"I'm excited for spring and the opportunity to finally show some skin. One of my favorite ways to do this elegantly is through footwear, so you can imagine my excitement when the boat shoe showed up at my door. The first time I wore this minidress was for a nice dinner, and I wore a pair of high heels and a mini bag with it. It's nice how versatile it can be because as soon as I threw on the Sperry shoes, the whole look was immediately perfect for a casual weekend. (The rawhide laces and contrast stitching give off that easy, laid-back vibe.) I love dressing from the shoes up, and since these are so comfortable, there are a million places I could take this look."

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Boots are to winter wardrobes as bikinis are to summer. I really can’t get through one chilly week, let alone the holiday season, without them. This year, I’m especially into the chunky-sole trend, which first bubbled up last year and luckily, has stuck around. I have my eyes on two particular styles from Sperry that I found at Nordstrom while doing a little winter shopping (as one does). I’m into these pairs for cold winter days, especially when the weather can be a bit less predictable than I’d prefer. One is a shearling lace-up style, and the other is a chunky Chelsea ankle boot. And don’t worry—I’m sharing exactly how I’d style them for every upcoming winter occasion.

Holiday Gift Shopping

While I’m not a fan of crowds, I am a fan of buying gifts in person. Sometimes you just need to feel a sweater to know if it’ll be soft enough for your mom, or you need to smell a perfume to decipher if it has just the right amount of floral notes for your best friend. Since a day of shopping in any city can be a bit hectic, I like to focus on my wardrobe to help me feel prepared.

My footwear must be warm and comfortable since I'll likely be on my feet for hours at a time, which is why I love these black shearling-lined, lace-up boots. While my gut says to wear the boots with denim, a matching-leather-pants-and-top situation feels a bit more luxe. Another nonnegotiable on a busy day is a crossbody bag that not only holds my sunglasses, hand sanitizer, and maybe even a snack or two (don’t @ me) but also allows me to be hands-free while picking out gifts.

Travel Day

I’m planning a ski trip with friends this winter, and I will absolutely be packing the Torrent Boots for the occasion (in both colors if you’re wondering). The traction on the sole means that even my clumsy self won’t slip, and the suede material is actually waterproof, so I won’t ruin my boots even if I do.

For my travel day to said ski destination, I’ll wear the boots to save room in my suitcase (and also so I’m ready to go upon arrival). For maximum comfort, I’ll pair them with a cozy knit set, a fuzzy jacket, and a shearling-trimmed travel tote that complements the boots pretty damn well, if I do say so myself.

Annual Gift Exchange

My childhood friends and I always do a gift exchange when we’re back home in late December, and the unofficial dress code is "holiday casual.” The crystal buttons on the sweater and the beaded bag give the look a festive feel, while the light-wash denim, rubber boots, and classic wool coat keep things a bit more low-key.

The ankle height of these Chelsea boots makes them the perfect candidate for all of my winter denim outfits, even more so on rainy days. Plus, I love that they come in a range of colors, including this black-and-purple combo.

Holiday Lights Tour

By mid-December, just about every house in my neighborhood has decorations up. I usually make a whole evening out of walking around with friends to judge—I mean look—at all of them.

These Chelsea boots are ideal for a night spent outdoors and are no match for a little evening rain or even unexpected sprinklers. (Hey, it’s happened to me before.) They look so cute paired with a sweater dress, but at night I’ll be extra bundled up with a coat and beanie, too.

If you've ever been caught wearing white sneakers in the rain or boots without any tread in the snow, then you understand the importance of practical footwear. I've found myself in both scenarios before and can confirm they are far from fun. (Please learn from my mistakes, friends.) This year, I'm prepping my winter shoe collection properly with boots from Sperry, especially since I'm planning to leave Los Angeles a few times to visit cold-weather climates. (See you soon, Colorado friends!)

I love Sperry's boots not only because they perform well in both rain and snow but because they're also cool and on-trend. Sacrificing style because the forecast shows a minor storm isn't really my thing, so a trendy shoe that can withstand the elements is key for me. And I'm not the only one who's shopping Sperry for winter—in fact, three fashionable women I love following from both coasts tell me they'll also be wearing Sperry boots this season. Ahead, see their must-have winter-boot picks and the outfit ideas to match.

Sam Elise lives in Boston, so she knows a thing or two about cold-weather outfits. While she says her favorite snow-day ritual is watching Harry Potter on the couch with endless snacks, when she does step outside, she'll definitely be wearing these chunky Sperry boots. "I love the overall chunkiness and durability of them," Elise tells me. "The inner lining is also unbelievably soft, like a fuzzy blanket for your feet, which is key in the wintertime. Any boot that can bring an element of style along with comfort and durability wins in my eyes."

True to her typical style, which she describes as minimal and edgy-chic, Elise pairs the lug-sole boots with a fitted jumpsuit and a sleek trench coat. The combo of casual and polished pieces feels really cool and elevated.

While Talia Hubble is also based in L.A., she's already taken her favorite Sperry boots for a spin on a recent trip. "I wore these all last week in Vermont with a ton of outfits, both casual and formal," she says. "The brown and white trim adds such an elevated detail. The boots are functional and chic."

The rubber material and warm micro-fleece lining makes the boots a perfect choice for cold, rainy weather, but the on-trend chunky Chelsea silhouette makes these worth adding to your closet whatever the weather. I might style these with leather leggings and a chunky knit, but Hubble's sweater-dress is so cute, too. (Just add tights when the temp drops.)

Duck boots are the OG of rainy-day footwear, so I was excited to see that Josie Francis chose this multi-color pair. Francis says the boots' olive and black colors inspired the earth tones in the rest of her outfit. (Side note: how good is that puffer vest?) "I'd probably wear this outfit to run errands or grab an afternoon coffee," she says.

What you might not notice at first glance is that these boots have a special sole created with enhanced traction as well as nylon water-resistant fabric. Plus, quilted fabrics in general are really having a moment right now. There's really no better choice for a rainy day, especially a cold one.

With spring right around the corner, especially here in always-sunny Los Angeles, I've been starting to make some major swaps in my wardrobe. Oversize puffer coats are getting replaced with more tailored blazers, chunky sweaters with lightweight knit dresses, and lug-sole boots with more spring weather-friendly footwear.

I'm specifically referring to three pairs of shoes I'll be wearing on repeat from a favorite fashion brand of mine, Sperry: canvas sneakers, leather boat shoes, and rain boots. They're all what I consider absolutely essential footwear additions to my personal spring wardrobe. There are endless ways to style these shoes, but the outfits below are topping my list at the moment.

There are few styles of footwear I wear year-round more often than white or off-white sneakers. During spring it's all about a canvas style. I'm particularly excited about this pair from Sperry because the laces are hassle-free. Yes, you heard me right: The barrel ties mean these sneakers just slip right on.

I can't really think of an outfit I wouldn't wear with these sneakers at the moment, but a breezy cotton dress is always a go-to of mine. This puffy-sleeve maxi style is equal parts trendy and classic just like the sneakers, making the two pieces a match made in heaven. Just add another white accessory to really make the shoes pop.

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My new black and white leather boat shoes are equally as easy to slip on and go. Are you sensing a theme here? This pair has the polished quality that you'd expect from this style of footwear but feels a bit more casual due to those same rope-style ties.

I love the pop of white from the rubber sole, so I styled these boat shoes with a head-to-toe black and white 'fit. (My fave color combo, no matter the season.) This zebra print miniskirt surprisingly gets a lot of use in my wardrobe, and right now, I'm pairing it with an on-trend leather blazer and ribbed tank.

SHOP THE SHOES

I never truly understood the importance of waterproof footwear until I lived through my first spring in New York (and all the romantic comedy-worthy unexpected rain showers that came with it). Now on rainy days, I rely on these duck boots like my life (or at least my morning coffee run) depends on it. Since pretty much every luxury brand is leaning into quilted fabrics right now, I immediately gravitated to this very on trend, elevated-feeling pair.

If styling duck boots feels a bit tricky at first, think about how you'd wear your favorite high-top sneakers. For me, that's with a lightweight and ultra-soft knit dress. I love the collar on this one, which has been a fashion-girl favorite detail for a minute now. For this look, I decided to add some knit socks and a leather baseball cap for good measure. Umbrella not pictured.

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Shop more spring must-haves from Sperry.

I don’t know about you, but I’m tired of boots that can’t handle a little moving and shaking. As someone who’s living, breathing proof that the whole "nobody walks in L.A.” thing is false (I will gladly proffer my iPhone’s step-counter data as proof), I require boots that knock the whole cost-per-wear algorithm out of the park, and given that I happen to work in fashion, said footwear’s also gotta look good. That means fast-fashion fixes are pretty much out, as are $$$ designer finds I’d be too worried about roughing up the first time I wear them.

The happy middle ground? I’m glad you asked. This season, I realized there’s actually one specific boot style that makes the grade where fall is concerned. Sperry’s Saltwater Duck Boots are classics that happen to be weatherproof (a must, even here on the West Coast—our rainy season is no joke), but there’s also something inherently street style about them, thanks to their interesting texture and shape. Need proof? Keep on scrolling to see and shop three fun, functional, trend-heavy fall looks I’ve put together—anchored, of course, by my boots of choice. Bookmark now and thank me later!

Stylish Yet Relaxed Office Attire

The Look: Scandi girls continue to be all-in on lilac, and that’s pretty much all you need to know. This look feels forward enough for a day at Who What Wear HQ, but it’s also plenty comfortable (super important come 3:30 p.m. when I’m trying to break through writers’ block!). I love the color clash we’re getting here with this very important (and very affordable!) Mango baguette bag and, more importantly, the texture clash with the duck toe on these Sperry boots.

Once Upon a Time… for a Night Out in Hollywood

The Look: I searched high and low for a pair of boots that would work with this incredibly fun, slightly retro-inspired night-out look I’ve pieced together for a friend’s birthday dinner (Night + Market on Sunset, here we come), but thanks to the two-tone color scheme and the look’s decidedly maximalist leanings, nothing seemed to work… that is, until I came across this excellent lace-up hiker style on Sperry’s website. A night-out look you can actually walk in? Into it, especially as our night out will likely lead us to bars a bit further down the Sunset Strip.

Desk to Drinks to Dinner (and Beyond?)

The Look: If you’ve booked a vacation to Los Angeles between November and, say, early May, I regret to inform you that the forecast might not entail the sunny skies you’ve been envisioning. As any Angeleno will tell you, things can go from 50º to 90º in less than 24 hours, so layers will be your BFF. Here, I’ve re-created one of my signature fall looks that effortlessly takes me from desk to drinks to dinner. (The walk from Who What Wear’s West Hollywood office to Cecconi’s is notoriously not fun in strappy sandals or high heels, y’all, especially in late November.)

That’s not all, of course—there are so many other great colorways we wholeheartedly endorse. Visit Sperry’s website to see and shop more duck-boot styles.

It doesn’t matter how old you are; as soon as summer is over and fall’s on its way, it’s hard not to feel nostalgic for back-to-school season. Stocking up on new bags, collecting supplies, and buying new clothes—specifically a first-day-of-school outfit—are all quintessential memories of starting class. Luckily, even if you’re not sitting in homeroom anymore, you can still take part and transition or update everything you have, just because you can. Where to start? Treating yourself to a few key essentials from Sperry, including a pair of comfortable and stylish shoes, which are not only practical but also extremely elevated, so you won’t be sacrificing comfort for style here.

Scroll down for four “back to fall” essentials from Sperry. 

Don’t let colder weather get in the way of wearing stylish shoes. Even though you have to be more covered up and it’s harder to get around town in crummy weather, there are options that are both comfortable and fun. Sperry has plenty of elevated picks—preppy vibes included—so you won’t feel like you’re sacrificing your outfit for comfort.

You don’t need to be a student to have a journal. In fact, having one with you at all times will not only keep you organised, but also help you remember all your ideas.

Fall and winter are all about layering, so having an assortment of shirts on hand is pretty much mandatory. You can never go wrong with a classic print, like stripes, or something neutral.

Everyone needs to own some sort of backpack. Whether you use it for travelling or toting your things around town, it’s necessary in the fall. You can throw pretty much everything in it without worrying that your valuables will be rained or snowed on.