4 Winter Shoe Trends For When You Can’t Bear A Boring Boot

Bella Gerard
4 Winter Shoe Trends For When You Can’t Bear A Boring Boot
Photo: Courtesy of Steve Madden; Sam Edelman; Louise et Cie; Adobe.

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My current Tiktok obsession is user Deanna Giulietti, known for sharing her outfit of the day, or ooh-ta-da, at the request of her adoring followers. “Back it up, back it up, peep the shoe,” she always says, “move it forward, move it over, peep the shoe.” The more I watch, the more I realize I really need to step up my footwear game, which is why I’m taking 2020 and 2021’s winter shoe trends so seriously.

OK, I’m kind of joking—Giulietti’s videos are just one of the many reasons I want to go shoe shopping. Another? This year’s trends are hella cute, and I don’t want to miss out. This season, there’s a wide variety of trending silhouettes and details, and you can dress them up or down. Chloé made rain boots cool again with a single pair, and now, tons of chunky, monochrome lug sole boots are taking over street style. On a daintier note, loafers are back, and you can decide for yourself whether you’re into more traditional workwear styles or creative, dressy takes.

Given that we’re all starting to feel some separation anxiety from our slippers, it’s no surprise that fluffy sherpa and faux-fur styles are trending, too—but not all the looks this season are casual and cozy. Chains and literal shoe jewelry are all the rage, so catch me layering anklets over my footwear until I can afford the shoes on this list.

With that, I’ll let you peruse the styles below to get a true feel for what’s hot right now. These winter shoe trends will help you start off 2021 on the right (very stylish) foot. Enjoy!

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STYLECASTER | Winter Shoe Trends

Courtesy of Sam Edelman.

Lior Loafers

Once reserved for frat boys and business interns alone, loafers are now a cool-girl staple, and they add boss betch energy to any outfit. For a basic, wear-everywhere style, try the Sam Edelman Lior Loafers in any of six shades.

STYLECASTER | Winter Shoe Trends

Courtesy of Louise et Cie.

Everland Loafer

For a dressier option, the Louise Et Cie Everland Loafer just went on sale, and I’m in love with the stylish chain detail—also a huge trend this season, but more on that later.


Chained Up

STYLECASTER | Winter Shoe Trends

Courtesy of Kurt Geiger.

Polly Pointed Toe Mule

Chain details started gaining popularity in fall, and they’ll definitely continue to be cool well into 2021. These Kurt Geiger flats are simple yet stunning, and the gold chains elevate the comfortable, everyday silhouette.

STYLECASTER | Winter Shoe Trends

Courtesy of Steve Madden.

Malvern Loafers

If you’re looking for something a bit chunkier, consider these Steve Madden loafers. A thick lug sole is huge this year, and these shoes are, well, also huge.


Fluffy Stuff

STYLECASTER | Winter Shoe Trends

Courtesy of Jeffrey Campbell.

Beagle Faux Shearling Mule

Given that we’ve been wearing slippers all year, it’s no surprise that fluffy, fuzzy goodness is trending. These Jeffrey Campbell loafers are two trends in one, and they’re basically a warm hug for your feet on a cold winter’s day.

STYLECASTER | Winter Shoe Trends

Courtesy of UGG.

Fluffita Slipper

If you want house shoes that you can wear to run errands, too, the UGG Fluffita Slippers are for you. These chunky sherpa flatforms are as funky as it gets, but trust me (yes, I own them!) they feel like heaven.


Lug Soles

STYLECASTER | Winter Shoe Trends

Courtesy of ASOS.

Aqum Chelsea Boots

When super chunky lug-soled boots hit the market, the fashion world went wild. Suddenly, wellies were seen as fashion-forward footwear, not thunderstorm necessities. You don’t have to go for rain boots, though—anything with a thick sole will do. Exhibit A? This pair by ASOS.

STYLECASTER | Winter Shoe Trends

Courtesy of Pretty Little Thing.

Cleated Sole Chelsea Ankle Boot

I’m not saying these Pretty Little Thing boots are a damn good dupe for the Prada ones, but…they really are.

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