I'm Obsessed With Wearing Boots RN, so I Styled 5 Pairs I Want in My Wardrobe

Sponsor Content Created With Sperry


(Image credit: @ellamiller)

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.

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.