The Warmest Hats Will Keep You Toasty All Winter Long

You ever notice how in any given group of friends there’s always one designated hat guy? You know the type. This is the dude who gets way too excited when beanie season rolls around each year, because it means he can finally swap out the sweat-stained baseball cap he’s been wearing for the last six months straight. You haven’t seen the top of this poor schmuck’s head in years and you’ve got a nagging suspicion he’s going to try and rock a 5 panel to your buddy’s wedding next summer. Fuck matrimony. That’s real commitment, folks. Being the hat guy isn’t a choice. It’s a lifestyle. (If you can’t think of who the hat guy in your group of friends is, I’ve got some bad news. Are you wearing a hat right now?)

These days, being a hat guy isn’t the worst thing in the world. Hell, over the years we’ve all flirted with the title. I, for one, went through a month-long stage in high school where I refused to leave the house sans what I hoped would become my signature—but alas, all too short-lived—accessory: a classic Boston Red Sox snapback I scooped on a family trip to Fenway Park. A gust of wind blew the thing off my head and into a lake four weeks into the endeavor and that was the end of that.

Winter, and this winter especially, is the best time to embrace your inner hat guy. We’ve long extolled the virtues of the humble beanie, but the seasonal hat-related excitement shouldn’t stop there! Why not rock a baseball cap (in a winter-ready wool or flannel) like you’re an old-timey big leaguer slowly plodding out to the field after conspicuously ripping half a pack of cigarettes in the dugout? Or fully freak it and reach for the type of furry trapper hat you might’ve worn if you were born a few centuries earlier to a family of rugged outdoorsmen (ha!) looking to hunt down an elk before breakfast. In this age of actor slash this and creative director slash that, why not be a man who literally wears many hats, no hyphen needed?

This winter, be the hat guy. Here’s where to start.

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Heattech Knitted Cap

Uniqlo uniqlo.com

$14.90

The retailer updates a bona fide wintertime staple using its signature heat-retaining material. The result? A handsome marled beanie that’ll keep you looking cool (and feeling warm) all season long. 

Denali Earflap Ball Cap

The North Face thenorthface.com

$35.00

A cheeky riff on the brand’s beloved outerwear silhouette, made with the same type of fleece that’s endeared the style to so many fans of The North Face over the years. 

Fisherman’s Rolled Beanie

Patagonia huckberry.com

$35.00

A responsibly made beanie cut from recycled polyester in the same shade of gold as the leaves outside. 

Wool Ball Cap

Arc’teryx endclothing.com

$35.00

The outdoor gear experts at Arc’teryx sweat the details so you don’t have to. The brand’s 6-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 either. 

Sun Rise Tie Dye Beanie

Parks Project nordstrom.com

$40.00

A hand-dyed, positively mind-blowing beanie perfect for any trip you take this season, psychedelic or otherwise. 

FlapJack Earflap Cap

Seager Co. huckberry.com

$45.00

Built-in earflaps take an otherwise good corduroy cap deep into “great” territory. 

USA National Team 1956 Vintage Ballcap

Ebbets Field Flannels ebbets.com

$49.00

Patriotism, so hot right now. Patriotism. 

Stock Polar Fleece Low Pro Cap

Stüssy endclothing.com

$55.00

What was once the stuffiest pattern in dear old dad’s closet gets a serious dose of youthful energy  of the design fiends at team Stüssy. 

Cord Bucket Hat

Carhartt WIP endclothing.com

$65.00

When done up in corduroy, the bucket hat—that trusty headwear staple of summers past—becomes the winter-ready accessory you’ll reach for time and time again. 

Dalegarth Hunting Cap

Barbour endclothing.com

$65.00

Made out of the same waxed cotton as the brand’s trustiest lightweight outerwear, with corduroy ear flaps for extra insulation.

NY Yankees Low Profile Cap

Todd Snyder + New Era toddsnyder.com

$68.00

Yes, the Sox fan in me is deeply pissed off that this hat—inspired by textiles sourced from Abraham Moon mills—came out looking so damn cool. The clothing enthusiast in me? Not so much. 

Sherpa-Lined Bucket Hat

David Catalán urbanoutfitters.com

$99.00

Because why not line your already solid bucket hat with the ultra-soft, high-pile fabric all of us swear by? 

Quilted Nylon-Ripstop Bucket Hat

Monitaly mrporter.com

$100.00

Cut from the same waterproof nylon-ripstop fabric that’s used to make parachutes (seriously!) and lined with insulating fill for added warmth.

Alpine Beanie

Palace urbanoutfitters.com

$115.00

A second chance at getting your hands on an all-time beanie style that first dropped as part of the British label’s fall/winter collection last year. 

Wool-Blend Jacquard Trapper Hat

RRL mrporter.com

$175.00

A trapper hat so authentic you could do some real trapping (*winks slyly*) wearing it. 

Printed Shell Bucket Hat

Dries Van Noten mrporter.com

$350.00

Blurred floral collages that reference the long, adrenaline-fueled nights of ’90s rave culture? Hell yes. If you’re really about the hat life, the style you wear this winter should double as art. 

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Avidan Grossman is the Style eCommerce Editor at Esquire, covering men’s fashion, shoes, grooming, and accessories.

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Source : Esquire