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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.
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.
Winter white ensemble in need of a pop of something? Chunky back boots and an equally chunky black blazer should do the trick.
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.)
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.
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.
Pair your beanie with cropped trousers and an oversized denim jacket, and you’re sure not to veer too far into skater territory.
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.
I’m becoming increasingly convinced that my mistake was in buying a black beanie and not a colorful one.
Why yes, that is a jacquard power suit paired with a beanie. I told you winter beanie sophistication was an option.
A reminder that beanies have an inherently streetwear vibe, and if you can make the most of it, you definitely should.
Because the only thing better than a logo-covered beanie is a logo-covered beanie paired with two animal print pieces.
Pop of color on your shirt? Accentuate it with an equally colorful beanie.
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.)
Colorful sunnies and winter beanies are a truly underrated combination.
I mean, why not2019’s favorite color sport in four ways at once?
Lace dress, meet beanie—your surprising new soul mate.
OK, beanies, red lipstick and gold hoops is my new favorite trifecta.
If your beanie matches one of your shirts, there’s no excuse not to wear them together.
When in doubt, try rendering your outfit in one palette and your accessories in another.
Striped beanies—with pom-poms on them—are definitely the new black.
Really digging every iteration of the all-white-ensemble-save-black-shoes-and-black-beanie movement I’m seeing.
It’s official—I need a colorful beanie, stat.
The more experimental you can get with streetwear, the better (assuming that’s your thing).
Because the whole beanie + trench coat + sneakers thing is a total classic.
A beanie and bow-embellished heels? A super-surprising match made in heaven.
If your beanie speaks for itself, you can probably get away with pairing it with anything.