26 Street Style-Approved Ways to Wear Your Favorite Winter Beanie

If you live in a place where the winters get absolutely frigid, you know winter beanies are an absolute must-own. But you probably also know the question of how to wear a winter beanie—or at least, how to wear a winter beanie fashionably—is a genuinely complex one. Because nothing ruins a sophisticated chic look—or a carefully coiffed hairdo, for that matter—like a winter beanie.

I’ve owned a beanie since I moved to New York three years ago, and I’ve yet to figure out how to style it. Cramming it on my head once I’ve already thrown an outfit together creates a disastrous motley crew of an ensemble, and letting my beanie lead the sartorial way always results in a kind of skater-streetwear aesthetic that I definitely don’t identify with. My winter beanie keeps my head so warm and cozy that I can’t bear to part with it, but the effect it’s had on my wardrobe is tragic, at best.

It was with hope in my heart that I turned to the street style-scape to see if fashion’s most creative minds had solved the seemingly unending dilemma of how to look cute in a winter beanie. And, true to form, they had. There were winter beanie outfits designed for every aesthetic—no matter how dainty, feminine or proper. The question of how to wear a winter beanie was no longer un-answerable—for me, for you or for anyone else who’d ever posed it.

STYLECASTER | 26 Street Style-Approved Ways to Wear Your Favorite Winter Beanie

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Keen on avoiding a bad hair day? Throw your go-to beanie over a side braid. Don’t own a go-to beanie yet? One in a pastel brown, like the one pictured here, offers versatility in terms of palette and aesthetic.

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Winter white ensemble in need of a pop of something? Chunky back boots and an equally chunky black blazer should do the trick.

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A colorful beanie is just an excuse to go full maximalist with the rest of your outfit. (Especially if you own a matching colorful scarf.)

Christian Vierig/Getty Images.

The most wearable answer to this question I’ve ever seen. Low-key, effortless, beanie-filled style is possible—and it’s staring you in the face.

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I’m genuinely obsessed with this high-fashion take on the beanie outfit. I wasn’t aware beanies could make be worn as statement pieces—until I saw one paired with red boots and a millennial pink tutu skirt and a bright blue faux fur collar.

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Pair your beanie with cropped trousers and an oversized denim jacket, and you’re sure not to veer too far into skater territory.

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Yup, even beanies have gotten in on the whole logomania thing. And since any singular logomania piece can carry an entire ensemble, I totally get it.

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I’m becoming increasingly convinced that my mistake was in buying a black beanie and not a colorful one.

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Why yes, that is a jacquard power suit paired with a beanie. I told you winter beanie sophistication was an option.

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A reminder that beanies have an inherently streetwear vibe, and if you can make the most of it, you definitely should.

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Because the only thing better than a logo-covered beanie is a logo-covered beanie paired with two animal print pieces.

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Pop of color on your shirt? Accentuate it with an equally colorful beanie.

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OK, so black beanies can combine with sweatshirts, jeans and sneakers to create something other than a skater girl look. Maybe all I was missing was the tailored trench. (And honestly, probably the glasses.)