Fashion Insiders From Coast to Coast Are Wearing These 3 Winter Boot Styles

Sponsor Content Created With Sperry


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.


(Image credit: @samanthaaelise)

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.


(Image credit: @talliia)

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.)


(Image credit: @josie_francis)

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.

Associate Fashion Director, Branded Content

Michaela Bushkin is the associate fashion director on the branded content team. She is based in Los Angeles and is going on her sixth year at Who What Wear. Michaela has always worked in the content world, previously at Whalerock and The Zoe Report. Her current role involves executing content, photo shoots, and events for fashion brands from retailers to luxury designers and everything in between. She spends her free time online shopping (or "researching" as she likes to call it), reading at the beach, and trying as many new restaurants in L.A. as possible.