For the longest time, winter hats—nay, hats en masse—didn’t really register with me. Man, if you saw the beautiful head of hair, which I meticulously coiffed every morning before school, you’d understand why. I liked showing off my best assets (still do, in fact) and covering them up didn’t make sense. Even during the bitterest of winters, when snowfall was near constant for months on end, all I would do is shroud my head with a hoodie, never tightening the drawstrings so as to keep my gelled side-part intact. Needless to say, I argued with my mother often. I also got sick often. My petulance always got the best of me.
Admittedly, I did gravitate toward berets for a hot minute, only because I started becoming a Francophile, which coincided with my discovery of Mary Tyler Moore. That phase didn’t last too long. Then, around the late ’90s, I became fascinated with newsboy caps, largely because of LL Cool J, who began wearing the style, almost exclusively by Kangol, post his bucket hat period and his pre his station in the land beanies. That was also a fleeting period.
Now, come winter, I wouldn’t be caught dead without my head encased tightly and securely in wool, cashmere, or something lined with fleece. Wisdom comes with age, and from experience, I’ll do anything to not be sick in bed, surrounded by bottles of DayQuil and NyQuil, cups of throat-soothing tea, and mounds of used Kleenex. If I do have to step out in the cold, I’ll take my pick from my closet of hats—from buckets and beanies to caps and berets—that are all made of insulating fabrics and materials. It’s about performance first and foremost, but that doesn’t mean I forgo style completely. And if you, too, learned the hard way about why wearing a hat in winter is a necessity (or maybe you just listened to your parents from the start), check out the 17 below that’ll keep you comfy, cozy, and, hopefully, sniffle-free.
Heattech Watch Cap
The retailer updates a bona fide wintertime staple using its signature heat-retaining material. The result? A cap beanie that’ll have you looking cool and feeling warm all season long.
Fisherman’s Rolled Beanie
A responsibly made beanie cut from recycled polyester in the same shade of gold as the leaves outside.
Wool Ball Cap
The outdoor gear experts at Arc’teryx sweat the details so you don’t have to. The brand’s six-panel wool-mix cap is a gorphead’s dream, though stamping it with the label’s iconic fossil logo front and center definitely doesn’t hurt.
Reversible Sherpa Bucket Hat
Why not line your already solid bucket hat with the ultra-soft, high-pile fabric all of us swear by? And, for that matter, why not have it be completely reversible, too?
Good Vibes Shroom Beanie
A shroom-printed, positively mind-blowing beanie perfect for any trip you take this season, psychedelic or otherwise.
Insulated Earflap Ball Cap
A cheeky riff on the brand’s beloved outerwear silhouette, made with the same type of nylon and fleece that’s endeared the style to so many fans of The North Face over the years.
Flapjack Corduroy Ear Flap Cap Red
Built-in earflaps take an otherwise good corduroy cap deep into great territory.
USA National Team 1956 Vintage Ballcap
Patriotism, so hot right now.
Mad Bomber Wool Hat
Large and in charge, this incredibly insulating fur-lined bomber hat is for those that like to stand out—the the best sense, of course.
Chili Piper Wool Blend Newsboy Cap
Peaky Blinders fans know what’s up.
Big Logo Low Pro Cap
Corduroy, always a cold-weather staple, gets the headwear treatment thanks to the streetwear masters at Stüssy.
A wide-brim hat, made of 100 percent wool, made for legit hard-and-fast ramblers.
Abstract Houndstooth Hat
Leave to the folks at Kangol to make the sometimes-suspect newsboy cap—in houndstooth, no less—cool again.
Wool Blend Beret
A French staple that proves why France is a fashion capital.
The Cashmere Rib Beanie
The warmest option from an always-reliable brand. You can’t go wrong with this beanie.
Cord Bucket HatBlack
When done up in corduroy, the bucket hat—that trusty headwear staple of summer—becomes the winter-ready accessory you’ll reach for time and time again.
59Fifty Adjustable British Millerain Ball Cap
A tartan plaid number, made of waxed cotton fabric, that’ll be all the rage on the 4 train, Yankee Stadium, and anywhere in the tri-state area, save (maybe) for Queens.
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Source : Esquire