winter layers
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Jetting from humid MIA (Miami) to frigid MSP (Minneapolis-St. Paul)? Or from dry, chilly DIA (Denver) to tropical SJU (San Juan)? Packing for winter travel can be a bear, and much trickier than the devil-may-care sundresses and shorts of summertime. Particularly when heading from one climate to another, you might wonder, “Do I really need a thermal layer? How about a fleece?

We have our own opinions on packing the perfect suitcase, of course, but this time we went to the all-weather pros: A Salvation Army bell-ringer in Wisconsin, a postman, a pro cyclist, a butcher, a cheesemonger, a UPS driver, and “Top Chef” judge Gail Simmons. Each is accustomed to changeable temperatures and humidity levels. Here are their (knockout) tips.

Terry Henderson, City Carrier, New York City Postal Service

“Neither snow nor rain nor heat nor gloom of night stays these couriers from the swift completion of their appointed rounds.” So read the words inscribed at a Manhattan USPS branch, and they’re apt; New York City is notoriously finicky, temperature-wise.

Of this unseasonably warm winter, city carrier Henderson laughs, “This is perfect; it could stay like this forever.” But over the last decade of delivering mail he has experienced temperatures as low as two degrees, along with snow, slush, and sleet. “Thank God for long johns,” he says today. Thermals, he says, are simply “a necessity.” He prefers the old-school white mesh thermals, and layers on a thick layer of those first, with a thin layer—usually a flannel—on top. Over that, he goes with a sweater, maybe a vest, and a hoodie. He pulls on two thick pairs of socks—“I know some guys who have the battery-operated ones!”—and comfortable boots. As for his head, he laughs, “In the army, they told us one of the best-kept secrets in the military: You’re so strong, but you have stockings on underneath!” He swears by a thin nylon stocking cap under a thicker hat.

Katie Compton, Champion Cyclo-Cross Racer

Champion American cyclist Katie Compton, who lives in Colorado, still struggles with proper layering, and says the key is whether you run hot or cold, and whether your environment is dry or humid. “You want to be warm but you don’t ever want to start sweating,” she says. “You don’t want to be wet.”

Layer to avoid that situation, and feel free to experiment with layers of various thicknesses. She’s a proponent of three layers, and swears by merino wool—Icebreaker and Patagonia are two favorites—and using a thin under-layer, a thick middle layer, and a windbreaker (for biking). For travel, she suggests comfy yoga pants, a sweatshirt or scarf for the plane, and wool. “If you can’t wash your clothing, it doesn’t smell as badly as cotton does. Sometimes with synthetics, they smell really bad.”

Elias Cairo, Butcher and Co-owner, Olympia Provisions

Portland, Oregon is notorious for its oft-changing, misty weather. Throw in the cold room where a butcher makes charcuterie, which is often around 35 degrees, and you’ve got a recipe for feeling cold fast. Asked whether he’s frequently layering up and un-layering, Cairo says, “Yeah, all my life!”

He tells his employees to always have a dry underlayer to keep moisture away from the skin (and keep the body from cooling down rapidly): “Thermals and wool socks are the keys to happiness.” He is a “sucker for Patagonia,” he says of the Capilene merino, which he thinks is “so expensive but it’s so much better.” He buys three of their thermal layers every year, layering a fleece and a sleeveless vest over them. When not at work, he’s a Pendleton wool fan, “because even if you get it moist, it’ll keep you warm.” He buys deerskin gloves at the hunting store, and invests in Red Wing boots, which he wears “to hunt, to work, and to New York City. I love ‘em.”

Captain Donald Karl, The Salvation Army

Captain Karl, ordained minister and longtime Salvation Army bell-ringer in Oshkosh, Wisconsin, has experienced temperatures below zero: “One has to do the layers.” He goes with flannel underwear, top and bottom, the complete SA uniform, a cap and earmuffs, and “really, really, really good insulated gloves.” When he takes a long car trip, he and his wife always pack extra gloves, hats, and boots. “You never know when you’re gonna have a malfunction.”

Zoe Brickley, Cheese Cave Manager and Sales Director, Jasper Hill Farm

Former cheesemonger Brickley lives in Vermont, and travels a good bit in her role at Jasper Hill. “It’s funny, but we do embrace wool up here,” she laughs. “Not sure if it’s a sensibility or what.” In the cheese cellars, wool is crucial because it wicks away moisture (in a moisture-rich environment). She and her colleagues are big fans of Ibex Woolies and Buff, which makes a “merino wool and stretchy neck thing” that, when it’s super-windy, “you can pull up” around your neck. When traveling, she swears by wool—a blazer that “looks smart in three seasons”— and a scarf.

Gail Simmons, “Top Chef” Judge

Having filmed in locales ranging from Alaska to Canada, Top Chef judge Gail Simmons—now judging the show in its 13th season—is a packing pro. “I always travel with a thin wool muslin scarf in a pretty print and thin heat tech gloves,” she emailed us. “The scarf is easy to throw on if weather gets cold, or on the plane if I need to layer or use it as a wrap, and it can brighten up any simple, neutral travel outfit.” She also likes that the gloves work while she’s on her phone—and that “both take up minimal space in my carry-on.”

Dan McMackin, Former UPS Driver

McMackin has been promoted from UPS driver to company spokesperson, but vividly recalls his time delivering packages in Wisconsin: “I delivered along the shore of Lake Michigan, where the wind would sting your face like a bull whip.” He and his colleagues would slather their faces in Vaseline for protection from the wind. “Your eyes would tear up and the tears would freeze on your cheeks; you’d peel off little shards of ice.”

If you’re being active, he suggests, “the biggest piece of advice is to wear layers and a base layer of something that breathes, like polypropylene. Wool or down are great insulators if you are sitting at a football game, but if you are moving and perspiring you need a base layer that breathes and wicks moisture.” His biggest mistake during one January deep-freeze was wearing weather boots with socks that didn’t wick moisture away; as he exercised, the sweat turned to ice. Nowadays, he’s lso a fan of “cheap, disposable chemical hand-warmers” and of proper hydration: “A hydrated body functions better in the heat and cold than one that is dehydrated.”