A Guide to Wearing Hats, According to the Best Winter Street Style of 2019

best winter hats for women

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To keep cool but stay warm during winter, you can’t skimp on great outerwear or outfit-making boots. The same goes for cold-weather accessories too: Because for the majority of the season, coats, boots, and, in this case, winter hats do most of the talking when it comes to bundling up while keeping things stylish. In order to break free from your standard winter-outfit formulas—and to keep your looks from looking like, well, everybody else—consider accessorizing functionally and fashionably this season. Here, find four headwear trends not to be missed, and shop 24 of the best winter hats, inspired by the most stylish women on the streets, from New York to Paris.

Buckets and Beyond

After runway debuts at Fendi and Loewe, the winter-ready bucket hat took over the streets last February—and this season the ’90s trend has continued to gain momentum. From shaggy faux furs to fuzzy angoras, from shearling to sherpa styles, the winter bucket hat is one of the cutest and coziest accessories of the season.

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Photographed by Phil Oh
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The Dreslyn Clyde Brown Fur Bucket Hat

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Charlotte Simone Billie Faux-Leather Bucket Hat

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Emma Brewin Classic Faux-Fur Bucket Hat

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Gigi Burris Eckers Felt Bowler Hat

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Urban Outfitters Suede Sherpa Bucket Hat

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Awesome Needs Classic Bucket Hat

World-Class Beanies

The ribbed-knit beanie has earned its place as a winter style staple for everyone from downtown urbanites to alpine skiers. New Yorkers might prefer sleek styles in a neutral color palette like black and speckled gray. Meanwhile, a pop of color would bring the perfect amount of joyous street-style-inspired Scandi chic to any drab winter look. And for those who wish to channel a bit of après-ski flair in their daily commute, look no further than one with a floppy, fluffy pom-pom.

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Photographed by Phil Oh
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Acne Studios Appliquéd Ribbed-Wool Beanie

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Other Stories Chunky Ribbed-Wool Blend Beanie

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Moncler Genuine Fox-Fur Pom Wool Beanie

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Vince Teddy Beanie

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Topshop Scandi Beanie

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Ganni Knit Beanie Hat

The Fashion Trapper

The trapper hat is no longer just for the rugged outdoorsman or Elmer Fudd. Not convinced? The trapper has been deemed stylish enough for even the Parisians—in fact a black faux-fur version was spotted on the streets topping off a geometric-print coat, leather pants, and blue ankle booties for the ultimate in warmth and style. Et voilà! Not to mention everyone from classic winter-weather brands to It labels are backing the trapper trend—Heurueh, Kule, and R13 to name just a few. You heard it here first: The trapper is the ultimate winter hat for women this season.

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Photographed by Phil Oh
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Cos Padded Hat With Ear Flaps

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Heurueh Luxe Faux-Fur Trapper Hat

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Kule Trapper Hat

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R13 Trapper Hat

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Kangol Faux-Fur Trapper Hat

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Ugg Long-Pile Sheepskin Trapper Hat

Wool Ranchers

On the other end of the headwear spectrum lies the wool rancher hat. Last season many showgoers in New York were spotted embracing this style—even in the ankle-high snow. Turn back time in one of these detective-style fedoras: They’ll look effortlessly cool with earthy-toned outerwear and mid-calf lace-up combat boots.

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Photographed by Phil Oh
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Avenue Mercer Faux Pearl-Embellished Wool Fedora

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Yestadt Millinery Harmony Ribbon-Trimmed Felt Hat

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Gigi Burris Georgia Rabbit Felt Fedora Hat

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Rag Bone Kacy Fedora

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Janessa Leone Edie Hat

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Lack Of Color Women’s Noir Rancher Fedora Hat