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A Man’s Guide on How to Dress for Winter Travel

The winter, it seems to us, is an ideal time to get away rather than hibernate. That’s why it’s so crucial you figure out exactly how to dress for winter travel. The equation is different for everyone, but for us, it involves that tricky-to-find mix of comfort, style and a polished appeal that’ll work on a plane, on a train, or … yes, in an automobile. So, we’re blending picks that are blends themselves: Of performance fabric and tailored silhouettes, of classic design and modern style. It’s that simple.

See for yourself and learn exactly how to dress for winter travel.

Naadam Mongolian Cashmere Hoodie – $295
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The first step in upgrading your winter travel ensemble? Reaching for a serious upgrade over the hooded sweatshirt you might normally wear. This cashmere hoodie is luxurious and comfortable without being overly heavy — the perfect layer for long hours in the airport or the car.

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Duer 9-to-9 Buttondown – $89
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Comfort mixed with polish is the name of the game with the aptly titled 9-to-9 Buttondown from Duer. It’s the rare dress shirt that doesn’t feel starchy or stiff. It’s made with cotton, COOLMAX fabric, and also spandex for stretch and, again, crucial comfort.

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Proof Rover Pants – $98
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Featuring the cut of jeans and the benefits of moisture-wicking fabric designed to stretch, the Proof Rover Pants are sure to quickly become a travel go-to. They’re much more polished than baggy sweatpants, too.

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Allbirds Men’s Tree Topper Sneakers – $115
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Don’t think you need to lug around or wear a heavy pair of boots for winter travel. These surprisingly lightweight high-top sneakers are breathable while keeping your feet cool and pulling together your overall look with casual-yet-sharp style. Plus, we love the deep red color.

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Darn Tough Standard Crew Light Socks – $20
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It’s the high-density stitch count that makes these socks so durable and easy to wear for travel. They look simple but sharp, they won’t slip or bunch, and they’re also anti-microbial. Get a few pairs in multiple different colors for all your winter travel needs.

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Jack Mason Diver Watch – $315
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The reliability of a dive watch can’t be overstated when it comes to travel, regardless of the season. The dive watch, especially this sharp number from Jack Mason, stands out in style on the road and wears just as well when you get to your destination. Count on it trip after trip.

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Stuart and Lau Monaco Weekender – $385
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The Stuart and Lau Monaco Weekender really is one-of-a-kind, thanks to the waterproof and lightweight construction. It’ll work for every trip this winter, complete with richly crafted detailing and leather accents — a stylish upgrade over your standard backpack, to be sure.

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W&P Design Carry-On Cocktail Kit – $24
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Travel should be fun, right? Not stressful. The well-designed and compact Carry-On Cocktail Kit series from W&P Design makes sure of that. We prefer the Old Fashioned option for a little in-flight luxury.

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If you’re looking for a winter coat to round-out this ensemble, check out our best parkas and rain jackets. You decide which one you need according to your travel destination.

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Beau Hayhoe
Beau Hayhoe is a freelance men's style writer, consultant and PR pro based in Brooklyn. Beau's menswear and gear writing has…
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