Topo Designs Merino Wool Beanie – $45
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.
Goorin Bros. Dutch Ellsworth Fedora Hat – $160
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.
Kangol Wool Flexfit Hat – $40
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.
Ebbets Field Flannels for J. Crew Brooklyn Eagles Ballcap – $50
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.
American Trench Cable Knit Cashmere Beanie – $110
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.
