Filson Watch Cap Beanie
There’s something to be said for consistently turning toward a brand that offers nothing but the best of the best across the board — and as you know, from flannel shirts to tough chore pants, that brand is indeed Filson. The Watch Cap Beanie is a worthy entry on our list and is every bit as reliable as you’d expect from this legendary company.
Finisterre Fisherman Beanie
If there’s one brand on this list of the best men’s winter hats that’s uniquely suited for the challenge, it might just be Finisterre — the brand’s roots as a surf-inspired company founded across the Atlantic shine through in terms of unique pieces like the Finisterre Fisherman Beanie, a rugged winter hat well-made for blustery Nor’Easter storms and cold temperatures inland, too.

Man winter hat
Just when you thought the lineup of the best winter gear at Huckberry couldn’t get any better, the brand comes through with its own beanie, the perfect encapsulation of what makes Huckberry so great.
When you need to gear up for your next demanding project on a cold, early winter morning, there’s probably one brand you’re wearing to outfit yourself — Carhartt. Complete that approach with the Carhartt Black Label Skull Cap, a tough-as-nails cap representing an even greater step up in style and quality from the classic, incredibly reliable Carhartt line.
“You’re well-aware of the fact that Orvis makes some of the toughest, most dependable gear on Earth when it comes to getting outfitted for the field or your next hunt — it should come as no surprise that they also deliver all the accessories you need for those pursuits, too”
By Beau Hayhoe
The North Face Standard Issue Beanie
The thing about gear from The North Face is that this legendary outdoor brand hardly ever makes anything that’s just “up to par” or in this case, “standard.” To wit: The North Face Standard Issue Beanie is dependable, well-priced, well-made and built to deliver in cold temperatures. The fact that it’s reversible also gives you two beanie caps for the price of one, and that’s something we applaud.