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How to Dress for Warmth and Still Look Cool

Channel your inner Jason Bourne with these fashion tips

Portrait of Matt Damon

Your mom was desperate. You were a boy, in the dangerous situation of being likely to encounter other boys. Which could mean snowball fights, sledding or that thing where someone tells you to smell snow and then they shove your face in it. So she swaddled you in as many layers as she could find.

Some of us are still putting on that same dumb winter outfit. I asked my fashion historian friend Kimberly Chrisman-Campbell what men should be wearing instead. “Wear whatever Jason Bourne would wear,” she told me.

I have a vague idea what she means — monochrome, dark colors, long coat, boots, pattern-free sweater — but it doesn’t look warm enough. So I reached out to Derek Guy, editor of men’s style website Put This On, for more guidance.

It’s all about the base.

Begin with a base layer, which is fashion speak for “underwear,” or more specifically, long-sleeved T-shirts and long johns. Guy suggests wool underwear, which is more breathable than synthetics like polyester and nylon and won’t absorb our awful winter man smells.

Woolx makes some of the warmest base layers, but Guy says Smartwool might be better if you’ll mostly be indoors and want to avoid Michelin Man lumpiness. When you’ve found the right base layer, the rest of your outfit doesn’t have to work so hard.

Do like that Led Zeppelin song and get into Kashmir … I mean, cashmere.

Cashmere sweaters, made from the winter undercoat of goats that originally came from Kashmir, have a reputation for being the best, and not just because they’re so soft. The fibers are finer than other kinds of wool, so they’re thin and they keep you warm.

They also last a long time — by some accounts, up to 30 years — and despite what some tags claim, you can hand-wash a cashmere sweater rather than dry-clean.

Though cashmere can be expensive, retailing for hundreds if not thousands of dollars, Guy assures me it’s easy to find a Scottish-made vintage cashmere sweater on eBay for around $40. Or buy a sweater made of Shetland wool, which Guy describes as “spongey, textured and very insulating.”

Your hands and feet need more protection than your head.

It’s a common misconception that we lose most of our body heat through our head. That’s wrong. Your hands and feet are actually bigger culprits in heat loss.

So forget the hat and look for something to keep your extremities nice and toasty. For your feet, this means boots. Find boots made for physical labor, not a ski trip. Brands like Timberland, Keen and Wolverine are comfortable, durable and won't slow you down.

Same goes for your hands. Avoid mittens for the obvious reasons (they look stupid, it’s difficult to maneuver your fingers, also they look stupid). Mittens are perfect for rolling snowballs, not finding your keys or paying for a coffee. Gloves will keep you plenty warm and they don’t say, “I’m getting a ride home with Mom!” Guy recommends leather gloves lined with… wait for it… wool.

Protect the neck.

Guy suggests popping your coat collar. Yes, like every villain in every teen sex comedy in the ’80s. A popped collar blocks wind from hitting your neck, and also apparently frames your face. Also, it lets the movie audience know that you’re the preppy bad guy who will probably lose in the end. 

A possibly better option: Wear a scarf. Something at least 64 inches long so you can tie it up and flip it around. Don’t overthink it; there are many ways to tie a scarf, but they’re all very twee and high fashion. Just throw it around your neck once and let both ends land on your chest, twice if it’s cold and your scarf is long enough.

If you get something with color to pop against a neutral-toned outfit, remember that these are the equivalent of wacky socks with a suit. Colorful patterns are fun; a message scarf proclaiming that “it’s hot toddy season somewhere” is not.

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