Hat & Headgear Styles for Winter

Winter is coming. In order to keep the cold out of your head, make sure to wrap it up in some of the most stylish hats and headgear. There’s a style for every fashion sense and temperature range, so be sure to keep a few in the closet just in case. Beware of the incoming hat head, because you’ll be wearing these styles all winter.

Beanie

The classic look for winter style, the truth about beanies is that they tend to be more hassle than they’re worth. Everyone has one lying around somewhere, and if you’re going strictly for style over substance, there are much better options to choose from. After all, unless your style icon is Stan Marsh from South Park, there’s not really anything new to be had with beanies. Still, they’re nice and warm, and fairly innocuous as far as winter fashions go. You could do way worse than going with a nice winter beanie.

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Bomber Hat

Again, think about who wears these kinds of hats. Canadians. The Scott Pilgrim’s of the world. If that’s the winter style you’re going for, by all means get yourself a bomber hat. It’s way more unique than a standard old wool beanie, and is invaluable if you live in an area  where winter brings unconscionable amounts of snow. But it’s also goofy as hell. Again, that’s not a bad thing, but it is the truth. If that doesn’t bother you, I say go for it. I wish I could see more people have the confidence to pull off a sweet bomber hat. 

Earmuffs

Pair your look back to only the essentials. If you want to keep your ears from freezing but don’t want to mess up your hair that took like an hour to dry this morning, there is a solution: earmuffs. Big, fuzzy, goofy, and playful, earmuffs are as practical as they are stylish, complimenting just about any outfit you might pull out when it’s snowing outside. Keep hat head out of your daily list of problems by skipping the hat altogether and instead pulling out the earmuffs next time the temperature dips below freezing.

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Backwards Snapback

Not explicitly a winter style, but more of a universal frat bro style ready for any season. It’s important to understand the subliminal messages that come with wearing backwards hats: “I’m perpetually 19 years old”, “I’m a big fan of Natty Light”, “My favorite sport is either cornhole or beer pong”, “I have no idea how to cook a meal and rely either on my girlfriend or Dominos pizza to not starve”. Stereotypes aside, the backwards snapbacks are still in fashion, especially if you’re in college. You’ll see them around, even when it gets cold enough to warrant something a little more substantial.

Driving Cap/Newsies Hat

Every single place I look calls this hat something different. If you’re selling newspapers on a New York street in the freezing cold winter of 1941, then this is a newsies cap. If you’re not a time traveler, you can call it a driving cap or maybe a beret or really whatever you want. Whatever you decide to call it, it’s a bold fashion statement that most people don’t have the nerve, or proper hat/clothing combination, to pull it off. If you’ve got a killer scarf/peacoat/boot outfit that needs a metaphorical cherry on top, try busting out this cap to complete the look and give you friends some advice on how to go bold with the winter accessories while you are at it.

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Balaclava 

For all your winter robbery needs. Apart from skiing or being caught in a blizzard, there really isn’t any practical use for a balaclava. It’s not stylish, it’s not sexy, but that makes it pretty cool. Especially in the COVID age, where masks are required every time you take a step outside, a balaclava is a perfect two-in-one hat/mask combo. Most of us look like armed robbers any time we walk into a place of business anyway, so why not lean into it and go for maximum warmth while you’re at it. 

Wide Brimmed Hats

Pros: you’ll get extra points for trying to look stylish. Cons: you’ll end up looking like a less-attractive John Mayer. There’s an essential scarf/hat combination needed to pull off this kind of look, and it’s definitely not for everyone, but if you can pull it off with a certain sense of style intact, you’ll be the sexiest looking rancher this side of Montana. Yeehaw.

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Scarf Wrap

Perfect hat alternative for non-hat wearers. It’s up to you whether you want to go full-on turban with your wrap, but even just a single wrap around will do wonders to keep your heat insulated. Scarves don’t just have to keep your neck warm, after all. They’re all super long for a reason. Wrap yourself up like a mummy if you have to. It’s all dependent on the weather outside. Baby, if it’s cold outside, wrap yourself up tight.

Santa Hat

‘Tis the season, and what better way to celebrate it than by decking yourself out in the most festive of all hats: the Santa hat. If you’ve got the gall to wear a Santa hat in a normal winter situation (i.e. not Christmas eve and/or not at a Christmas party) then you’ve probably got enough confidence to pull off just about any kind of winter style. If earmuffs were goofy, Santa hats are downright ridiculous. But they’re ridiculous in the best kind of way. Show your friends how to be fashion forward with a throwback to a winter classic.

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Holden Caulfield Hat

Be prepared to quote from everybody’s favorite 8th grade English assignment if you decide to go in this direction. The Holden Caulfield hat isn’t that much different from some of the other hats on this list: it shares some notable similarities with the bomber hat. But the major draw is attracting nerds. If that’s on your holiday season wish list, then this is the hat you should be shilling out for.