Accessorize With a Winter Hat for Warmth and Style

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Honestly, I love hats. I say it like a confession, but at the end of the day, what isn't to love? They are, perhaps, the most functional of fashion accessories, providing warmth through cold months (and, if you're a summer hat person, shade in sunny months). They tie together an outfit, and make even the baggiest and grayest of winter fits seem somewhat intentional.

To gear up for the cold months ahead, it's imperative you have a trusty hat at your side (or on your head, rather). All the greats have—just think of, I don't know, Holden Caulfield's red hunting hat, or Willy Wonka's top hat, or, if you really want to, Paddington's bucket hat (which, by the way, he chicly pairs with a periwinkle duffle coat).

Winter hats need to be warm, sure, but you don't have to sacrifice style to get there. For instance: look at Lululemon's warm and sleek beanie, or Canada Goose's aviator hat, or the sherpa cap from L.L. Bean that you'll want to wear until the heat of summer simply won't let you anymore. For rain, snow, and sleet, we've got you (and your head) covered with 25 of the best winter hats below.

Ribbed Knit Cap

Whirlibird Watch Cap Beanie

Fleece Lined Winter Hat

Ribbed Watch Cap

Cuffed Winter Hat with Fur Lining - 2 Pack

Cuffed Beanie

HEATTECH Ribbed Beanie

Haven Bucket Hat

Jim Beanie

Essential Ribbed Cashmere Beanie

Squall Sherpa Fleece Lined Winter Hat

Mad Bomber Supplex Hat

Fleece 2-In-1 Hat

This multifunctional Carhartt hat covers your head and your ears and also your mouth. The fleece is nice and warm but not too heavy.

Winter Duckbill Running Cap

When in doubt for good outdoor gear, Patagonia usually does it right. This duckbill cap has extended fleece sides to keep your ears warm.

The Organic Cotton Chunky Beanie

Everlane doesn't fail when it comes to reasonably priced, well-made stuff of everyday. This beanie is expertly chunky and the thick foldover ribbing is like a little hug for your ears.

Sheepskin Trapper

Not only does sheepskin lining and suede outer look cool but it also keeps the heat you want in and the cold you want out.

Sherpa Five-Panel Hat

This sherpa hat is the new best thing about fall. It's warmer than your summer baseball hat but not as warm as, say, a trapper is.

Winter Bucket Hat

For cooler days that aren't quite frigid, Adidas made a winter version of its classic bucket hat. The shape is done up in a winter-appropriate fleece.

PRO Insulated Beanie

This Orvis beanie is like your favorite puffer jacket, only for your head.

City Trek Heavyweight Beanie

For solid winter hats that will last for years, the outdoor experts at Columbia make the perfect heavyweight beanie.

Fine-Knit Hat

For something easy and cheap, scoop a beanie from H&M in an ever-rotating selection of colors.

The Lid

SmartWool hats are one of the smartest winter purchases you will ever make. The fabric is engineered to be thin but keep you just as warm as something with a heavier weight.

Warm Revelation Beanie

When it's winter, opt for a little bit of extra warmth—preferably without sacrificing style and comfort. This wool-blend beanie has the best of both worlds.

Logo-Embroidered Camouflage-Jacquard Wool Beanie

In thick and stylish wool, Celine Homme is bringing camo back this winter.

Faux Shearling Trapper Hat

If Holden Caulfield lived in 2023.

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