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A Gentleman’s Guide to Winter Socks


Gentlemen, it’s time to start thinking about your socks. (Please, contain yourselves.)

In a scant few weeks, your toes are going to be facing some decidedly brisk conditions, and it’s going to get a lot worse before it gets better. To that end, we suggest picking up the sock equivalent of a work boot, something that can protect your toes through just about whatever Mother Nature throws your way. And as luck would have it, we’ve got three candidates in mind…

The Casual Upgrade: This pair is essentially a thicker version of the high-top socks already in your drawer. That might sound like weak tea, but it means they won’t look out of place if you’re wearing them with something less than winterized. It’s an upgrade, and one your feet will most definitely appreciate, but it’s still within the range of things you could wear underneath wingtips. Of course, if you need something stronger…

The Chunky Foot-Sweater:As you might expect, the makers of the bean boot also make a pretty good wool sock. This L.L. Bean pair goes the natural route with non-itchy merino wool—giving it roughly the same feel as your favorite sweater. It’s bulkier than it is warm, but when you’re balancing winter treks with office duty, that’s not such a bad thing.

The Not-Screwing-Around Warmest Thing You Can Possibly Put On Your Feet:All three of the items on this list have a hiking history—that’s who’s usually stomping around in the cold, after all—but these smartwool socks are what most contemporary hikers actually wear, for the simple fact that they’re amazing. They’re as warm as you might want, and the synthetic fabric means they never get too swampy. They’re heavy-duty stuff, so you’ll want to save them for the day you break out your work boots. It’s sooner than you think.