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Our Picks to Upgrade Your Winter Hat Game for Every Situation

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Your winter hat game needs an upgrade — like, to one of the best men’s winter hats specifically. There are all kinds of styles out there to top off your ensemble, from the classic (and winter-friendly) fedora to a durable beanie cap to a stylish flatcap. We’ve picked out a few of our favorites below, each of which can team with winter style essentials that you already know, love and consistently wear — how about that? Shop away, and don’t forget to throw on one of these beauties the next time you leave the house.

Topo Designs Merino Wool Beanie – $45

Topo Designs Merino Wool Beanie
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What’s perhaps the number one hat you need in your wardrobe (and on your head) this winter? A dependably made beanie cap, one that simply gets the job done. The Topo Designs Merino Wool Beanie is your answer — no messing around with this piece, assuredly one of the best men’s winter hats out there. 

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Goorin Bros. Dutch Ellsworth Fedora Hat – $160

Goorin Bros. Dutch Ellsworth Fedora Hat
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Does your winter ensemble deserve something a little more tailored? Something a little more old-school cool and refined? The Dutch Ellsworth Fedora Hat, while not for everyone, is absolutely the right pick — wear it with a herringbone topcoat and a navy flannel suit for style that blends the throwback and the current.

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Kangol Wool Flexfit Hat – $40

Kangol Wool Flexfit Hat
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Kangol has been making instantly recognizable classic hats year after year without fail — the timeless, easy-to-wear Wool Flexfit Hat would look right at home with everything from a denim jacket and a henley to a shawl collar cardigan, slim chinos and beat-up leather boots. It’s a classic that’s right at home on any list of the best men’s winter hats. 

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Ebbets Field Flannels for J. Crew Brooklyn Eagles Ballcap – $50

Ebbets Field Flannels for J. Crew Brooklyn Eagles Ballcap
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You can still keep your trusty ballcap around for the winter months, especially if it’s a vintage-inspired number that’s easy to style with everything from a topcoat and jeans to a crewneck sweater and slim joggers (don’t forget leather sneakers). Does a ballcap deserve to sit on this list of best men’s winter hats? It sure does. 

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American Trench Cable Knit Cashmere Beanie – $110

American Trench Cable Knit Cashmere Beanie
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When you want to go really luxe with your winter headwear — as in, the type of option you could even wear with as a complement to a blazer and chinos — this reliable, well-made (and yes, pricey) cable knit cashmere beanie offers texture, visual interest and sharp looks.

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Beau Hayhoe
Beau Hayhoe
Former Contributor
Beau Hayhoe is a freelance men's style writer, consultant and PR pro based in Brooklyn. Beau's menswear and gear writing has…
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