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In case the pitch-black darkness at 5 PM didn’t already tell you, winter is basically here—and it’s time to grab your coats and start dressing for it. Is the cold sort of depressing? Yes. Do we have new Adele and the 10-minute version of “All Too Well” blasting on repeat until further notice? Of course, bring on the pain, baby. But the good news is that we can grab some tiny morsels of serotonin and warmth through layers and layers of winter fashion. While we love our winter boots and gloves, beanies and hats are the real unsung heroes of our winter wardrobe. Throw the right one on with a coat, and suddenly you’re exuding all the cool-girl vibes while still keeping warm and toasty? Yes, pls.
If you’ve already mastered the art of how to wear a beanie, good news: this season’s winter hats go way beyond cute beanies. There are faux fur bucket hats that will instantly transform you into a Hadid sister, cozy shearling baseball caps that scream “I don’t know what baseball is, but I am chic!!!!”, and leather hats that will make you look like a ’90s It girl. And if you’re simply looking to revamp your beanie collection, there’s plenty of good options there too. Aside from hiding a bad hair day, winter hats have the power to make any look instantly more pulled together, and something about wearing one just exudes Main Character Energy™—don’t ask why, I don’t make the rules.
In the spirit of keeping warm and still looking cool, here are the best winter hats—from classic cashmere beanies to on-trend fur bucket hats, shearling caps, and even a knit balaclava. Happy shopping!
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This Shearling Bucket Hat
Amara Faux Shearling Bucket Hat
There is no better way to keep cozy this szn than with a shearling bucket hat. All the cuteness of a teddy bear meets all the coolness of your fave model off-duty.
This Classic Cashmere Beanie
Ari Unisex Beanie
You can never go wrong with a classic black beanie, and this one is made of 100% cashmere, making it an extra luxe and warm addition to your winter wardrobe.
This Faux Fur Bucket Hat
Animal Print Furry Bucket Hat
Serve up an instant lewk in this trendy lil fur bucket hat. Available in over 30 different prints and colors, there’s a perfect match for every type of style this season—from animal prints to stars and stripes. Beware: major Main Character Energy will occur.
This Chic Fedora
There’s something so sleek about a wide-brim fedora paired with a wool winter coat that’ll make you look instantly polished and pulled together. Nobody will ever suspect you’ve got the 10-minute version of “All Too Well” blasting on repeat in your AirPods 😅.
This Street Style Staple
Logo Rain Bucket Hat
This Off-White bucket hat will transform you into a street style star—even if you’re only running to Trader Joe’s.
This Pom Pom Beanie
Knitted Beanie Hat with Faux Fur Pom
Fact: nobody can resist a furry pom hat. This affordable find from Amazon is no exception.
This Shearling Cap
Addison Faux Shearling Baseball Cap
Sports? You don’t know her. Winning at winter accessorizing in this shearling cap? Home run, touchdown, whatever—it’s an instant win.
This ’90s Bucket Hat
Vegan Leather Bucket Hat
Transform into the ultimate ’90s It girl in this vegan leather bucket hat that’ll pair perfectly with all your warmest winter coats.
This Ribbed Beanie
Heist Beanie Hat, Coyote Brown
The ribbed beanie is a staple, and this one’s available in a range of winter-ready colors perfect for bundling up in style.
This Leather Baseball Hat
Faux Leather Baseball Cap
More leather, more pretend sports, more style points to be won. Throw this baseball cap on while running errands for that ultra-cool incognito mode that’ll keep you ~mysterious~ and chic.
This Burgundy Felt Hat
A hat to match your glass of Pinot Noir? Why, yes, of course.
This Shearling Beanie
Embrace your inner teddy bear in this ultra-soft and cozy beanie that looks much more expensive than it’s price tag.
This Suede Cap
Jeremy Baseball Cap
Chances are you’ve probably scrolled past a ton of influencers looking v chic in Anine Bing on the ‘gram. Perfect for a touch of minimalism, the brand’s suede logo baseball cap is ideal for that effortless cool girl vibe.
This Knit Balaclava Mask
Wool Knit Balaclava Hat and Mask
A mask and a hat all in one? Tis the season!! There’s no better time to embrace the balaclava than this winter to keep warm and double-masked up.
This Clueless-Approved Hat
Check-Print Flannel Bucket Hat
A classic winter print that channels our favorite ’90s movie?
As if! Yes, pls!!
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