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

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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

Edward Berthelot/Getty Images.

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.

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

Gotham/Getty Images.

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

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

Christian Vierig/Getty Images.

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.)

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

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.

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

Timur Emek/Getty Images.

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.

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

Vanni Bassetti/Getty Images.

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

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

Christian Vierig/Getty Images.

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.

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

Melodie Jeng/Getty Images.

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

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

Christian Vierig/Getty Images.

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

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

Jeremy Moeller/Getty Images.

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

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

Christian Vierig/Getty Images.

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

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

Jeremy Moeller/Getty Images.

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

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

Christian Vierig/Getty Images.

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.)

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

Christian Vierig/Getty Images.

Colorful sunnies and winter beanies are a truly underrated combination.

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

Christian Vierig/Getty Images.

I mean, why not2019’s favorite color sport in four ways at once?

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

Christian Vierig/Getty Images.

Lace dress, meet beanie—your surprising new soul mate.

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

Kirstin Sinclair/Getty Images.

OK, beanies, red lipstick and gold hoops is my new favorite trifecta.

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

Timur Emek/Getty Images.

If your beanie matches one of your shirts, there’s no excuse not to wear them together.

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

Christian Vierig/Getty Images.

When in doubt, try rendering your outfit in one palette and your accessories in another.

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

Christian Vierig/Getty Images.

Striped beanies—with pom-poms on them—are definitely the new black.

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

Edward Berthelot/Getty Images.

Really digging every iteration of the all-white-ensemble-save-black-shoes-and-black-beanie movement I’m seeing.

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

Christian Vierig/Getty Images.

It’s official—I need a colorful beanie, stat.

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

Matthew Sperzel/Getty Images.

The more experimental you can get with streetwear, the better (assuming that’s your thing).

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

Christian Vierig/Getty Images.

Because the whole beanie + trench coat + sneakers thing is a total classic.

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

Christian Vierig/Getty Images.

A beanie and bow-embellished heels? A super-surprising match made in heaven.

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

Christian Vierig/Getty Images.

If your beanie speaks for itself, you can probably get away with pairing it with anything.

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