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Help Me Dress Myself: How to Look Good in the Rain

According to people from the rainiest cities in America

Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? Sick of condescending fashion articles telling you why you need to buy $200 T-shirts? Just want to know how to look, well, good? We feel you. Welcome to “Help Me Dress Myself,” an advice column for men who just want some practical advice for not looking like crap.

The Question

When it rains, it pours—and when it pours, I have no idea how to look good while also staying dry. I’m terrible at picking out raincoats: They always make me look like I’m setting off on the Appalachian Trail, when I really just want to walk the few blocks to work without getting completely soaked. Even worse, my hair ends up looking like a storm-battered tumbleweed. Help a guy out!

The Expert Advice

Cover the Basics. It should go without saying, but outerwear is king on rainy days, since it will keep the rest of your clothing dry no matter what you’re wearing. “I have two pieces that are critical to keeping me dry: Kamik Yukon Duck Boots and a Patagonia Torrentshell Jacket,” says Portland resident Colin Robson. (Portland experiences an average of 154 rainy days each year.) “Under that, I wear a flannel, a T-shirt and jeans—I tend to run hot, which means I need garments that aren’t too thick lest I sweat through everything (making things even more wet).”

Protect Your Hair. Don’t let the rain ruin your freshly-styled mane. “I always wear a hooded jacket—just in case it starts raining out of nowhere,” says Seattle resident Laine Hammer (like Portland, Seattle experiences an average of 154 rainy days each year). While most raincoats have a hood, Hammer specifically recommends North Face and Columbia (like Robson, she also suggests investing in at least one thinner jacket for warm—but wet—days). “I also wear a beanie or a hat—backwards, of course,” says Robson, adding that this is a good way to prevent your hair from becoming frizzy due to the humidity.

Preserve Your Pants. While pants tend to be less of a problem so long as you’re wearing the proper shoes, Robson recommends investing in fenders (or mudguards) if you’re a cyclist. “Those would keep my pants from looking like I just shit myself,” he explains, referring to the fact that fenders prevent mud and water from kicking up onto your clothes while biking. (Extra tip: Dark-colored pants are ideal for rainy days, since they’re less likely to show mud and wetness.)

Don’t Forget Socks. Wet feet are the worst, and while solid shoes (like duck boots) should prevent moisture from reaching your toes, thick socks are equally as important. “Smartwool socks are 100 percent the best,” says Hammer. “They’re warm and come in various types (thick, sport and so on). They also last forever!”

Prepare for the Worst. If the weather report says it’s going to rain, but there’s not a single cloud in the sky, still don’t be tempted to leave your rainy-day gear at home. “Keep a rain jacket in your bag at all times,” Hammer recommends. “Nobody uses umbrellas—at least in Capitol Hill (Seattle), where I live.” This means you’re shit out of luck if you head out unprepared, because nobody will have an umbrella for you to mooch off of.