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A Gentleman’s Guide to Winter Hats


On the heels of our tireless survey of the sock world, we thought we’d take a look at winter hats. These aren’t for decoration; they’re for that rare time of year when going out of doors uncovered is practically an invitation to frostbite. So in the interest of protecting both your earlobes and your sense of style, here are three of the best.

The Gentleman Traveler Borsalino This one’s the sophisticate of the group, sporting a full brim and a stiffly shaped body that makes those earflaps almost an afterthought. If you’re sporting an overcoat and tie—and modeling your style after a Florentine gentleman of leisure—this is your best bet by far. It’s not the warmest thing on the list, but it splits the difference between formalwear and arctic bundling just about perfectly.

The Toque Saint James Most of the hats you’ll see out there are simple single-roll wool caps, but there’s still room to make them interesting. Given the options, we suggest something as simple and as classic as possible, like this St. James version. Unlike the flock of other wool hats, there’s almost no chunkiness here—just a slick swath of fabric and an instantly recognizable nautical stripe. It’s thick without being bulky, giving you exactly as much fabric as you need and no more. In some circles, they call that elegance.

The Bicyclist Engineered Garments This entry from Daiki Suzuki takes after the classic bikers cap, including a clipped brim and almost invisible earflaps. And more importantly, it’s understated enough to pull off sans bicycle (swapping neon orange for black will do that). If you’re looking for an offbeat approach to winter, you’ll be hard-pressed to do better than this.