Best Winter Hats for Men
From Beanie Caps to Ballcaps, There’s a Hat for Everyone on the Market
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Make no mistake about it: Winter’s worst weather can be demanding in every which way, including the toll it takes on your wardrobe. But the best winter hats for men check off one crucial box — keeping your noggin dry, your ears protected and your face sheltered (somewhat) from the cold.
While beanie caps and fisherman caps have real-world heritage and modern-day utility, there’s a style of winter hat out there for everyone. Watch caps earn their stripes (especially in wool and tweed) when paired with a refined topcoat, and the classic stocking cap should prove useful just about any day of the week. And if you simply can’t get enough of the iconic ballcap style, rest assured that outfitters have turned their talents towards making winter-friendly versions of those, too.
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The best winter hats serve a purpose, but style points are every bit as important. Here are a few selections that, in our experience, hit the mark in both categories when it comes to your search for the best winter hats for men.
Filson Watch Cap Beanie

Call it the original, call it the best, call it what you will — Filson’s Watch Cap Beanie has very nearly seen it all, as the Pacific Northwest outfitter helped explorers brave the cold in the Northern Territory and beyond. Today, it’s a thick, tightly knit option made from USA-sourced wool for plenty of comfort in awfully cold weather.
Huckberry Logo Beanie

If you can trust one retailer to properly outfit you for adventures near and far, it just might be Huckberry. They make plenty of outdoor-approved gear, including a subtly stylish take on the beanie cap. Its wide-ribbed design is complemented by a fabric blend that includes nylon and spandex for performance, and the Huckberry logo tag — plus a wide array of color options — are never bad to have in your arsenal, either.
Patagonia Fisherman’s Rolled Beanie

Your winter hat rotation just got a little more sustainable, thanks to Patagonia’s use of recycled polyester in this tightly knit, classically styled beanie cap. It’s practically made for cold-weather pursuits (any winter sport you can think of), and its rib knit design ensures a snug fit – in any of its stylish color options, no less.
Flint and Tinder Tweed 5-Panel Hat

One of the more sartorial fabrics out there — houndstooth, often used to craft plenty of classic blazers — gets a shot at becoming more casual, yet no less versatile, in this new twist on the five-panel hat. Crafted by Huckberry’s Flint and Tinder line to pair with its expertly cut denim shirts and shackets, it’s a winter-friendly ballcap made with the utmost care.
Ebbets Field Black Wool Vintage Ballcap

Some hats earn their stripes in the spring and summer, and others are made for the demands of cold weather, in matters of both style and fabrication.That might sound like a tall task when it comes to the best winter hats, but the timeless design of this Ebbets Field cap speaks for itself, especially in thick, goes-with-anything black wool for a dash of vintage style.
Carhartt Wool Blend Patch Cap

If you’ve got designs on taking on a winter to-do list — and even if not — a wool ballcap can serve a dualfold purpose, keeping the weather out of your eyes while serving as a casually rugged accessory the rest of the time (say, for beers at your favorite dive bar). Carhartt workwear tends to fit both of those situations, and this toasty wool ballcap even features the brand’s iconic logo.
Boston Scally Original Cap

Long before “Peaky Blinders” brought the newsboy cap back to prominence, there was Boston Scally, and its focus on classic hats for men. Its newsboy cap plays on classic styles found across the pond, with fashionable grey herringbone fabrication. It should pair perfectly with a navy peacoat on a blustery winter day.
Stetson Reid Wool Flatcap

Stetson might be best-known for its Western heritage and stylings, but its version of the flatcap is refined enough to dress up. Made with wool and cashmere, it looks more polished than a newsboy cap (note the elongated design and shorter brim). Its understated design even pairs nicely with your best winter tailoring on snowy nights.
Cole Haan Newsboy Cap

The best winter hats for men should lend as much style and confidence to your #OOTD as they do functionality, and a newsboy cap or flat cap does a bit of both. Ideal to wear while driving or strolling around the city, this wool-blend option both regulates your temperature and shields your forehead from the elements — and it’s, of course, a debonair style move for the refined gentleman.
Home Prefer Felt Fedora

The fedora, although a time-honored style, is a particular look not quite everyone can pull off. But if one should strike your fancy, opt for a tried-and-true silhouette in winter-minded wool felt construction. This option is timeless, eye-catching and suitably stylish enough to pair with your topcoat and dress boots on a snowy night (along with the winter suit underneath, of course).
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