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What to Wear When Traveling

Everything you need on the worst day of the holiday season.

Man outside airplane hanger Photo: Neil Stewart/Trunk Archive

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If we’ve learned anything from celebrities, it’s that showing up to the airport in style is up there in importance with finding a good slice of avocado toast.

To your fellow commuters at the airport, you could be anyone: an international man of mystery headed to some hard-to-pronounce destination, a TMZ paparazzi target, or at least someone who’s getting some credit card points out of this whole ordeal. So why be the person who is so clearly dressed for a coach flight to the middle of nowhere?

Here’s a starter pack — considering every aspect of your travel day outfit — for those looking to impress, from departure to arrival, in coach, business, and first class.

Gucci loafers Photo: Kirstin Sinclair/Getty Images

Shoes You Can Slip On and Off

Taking your kicks off at security is inevitable, so at least be prepared with something you can get in and out of easily.

Coach: The Vans Slip-On ($50) is an obvious choice here (it’s in the name!) — choose a pair in your favorite color and get ready to fly through security.

Business Class: If you’re looking for more support and style on your next flight, grab these Adidas UltraBoosts 3.0 ($180) in all white. It’ll be like walking on clouds before you’re flying through them.

First Class: The Gucci Horsebit Loafer ($640) is a shoe so pretty, you might get held up at security while the TSA agents “inspect” them.

Man in T-shirt Photo: Edward Berthelot/Getty Images

Comfortable Top

As much as this is about looking good, the realities of flying make comfort imperative. Find a shirt that would make losing your luggage feel like a minor inconvenience rather than the end of the world.

Coach: You can’t really go wrong with a J.Crew Broken-In T-Shirt ($25).

Business Class: The Aimé Leon Dore Airport Sweater ($255); this feels pretty self-explanatory.

First Class: The Elder Statesman doesn’t call it the “Favorite Tee” T-Shirt ($470) for nothing. It’s 70 percent cashmere, 30 percent silk, and will probably make you 100 percent as comfortable as popping an Ambien before takeoff.

Man wearing Thom Browne sweats Photo: Melodie Jeng/Getty Images

Comfortable Bottom

Thank the fashion gods, because they’ve made it not just appropriate, but stylish to wear comfortable sweatpants while traveling.

Coach: Not even cramped seats could make these Alternative Apparel Blitz French Terry Pants ($54) uncomfortable.

Business Class: The John Elliott Escobar Sweatpants ($185) are what Scott Disick would wear to/from the airport. You deserve that.

First Class: You’re not really flying in luxury unless you’re in Thom Browne’s Tapered Striped Loopback Cotton-Jersey Sweatpants ($590).

Street style man in hoodie Photo: Christian Vierig/Getty Images


Traveling, for most, means changing temperatures a lot, from the frosty outdoors to the stale air of the plane. Equip yourself with something comfortable and versatile.

Coach: COS’s Wool Zip-Up Jacket ($125) is the brand’s take on a track jacket — zip it all the way up to the top while braving the elements.

Business Class: The Nike Tech Knit Bomber Jacket ($250) is made out of the same material used on the Beaverton, Orgeon-based company’s famously comfy sweatpants. As a bonus, it also ventilates in areas of your body that regularly get hot.

First Class: I’m tempted to cancel my flights and send back all the presents I bought for people just so I’ll have the cash to buy this Noah Baby Camel Hair Hoodie ($628). It’s perfect for flying: Camel hair is waterproof, windproof, and thermostatic, meaning you can wear it in both warmer and chillier climates.

Man with bag street style Photo: Melodie Jeng/Getty Images


Bags so nice you’ll start shouting, Ben Stiller-style, “bomb bomb bomb if someone tries to check it for you.

Coach: This Ted Baker London Yusaf Duffel Bag ($115.99) punches above its weight. Handsome bags at just over $100 are not easy to come by.

Business Class: A Filson Twill Duffel Bag ($395) will say that you’re off on a daring adventure, even if the only physical challenge you’ll put your body through is overeating all the home cooking.

First Class: Bric’s Bellagio 21" Carry-on Spinner Trunk ($550) — because you’re rich AF and you want everyone to know it.

Man wearing headphones Photo: Edward Berthelot/Getty Images


Topping off an outfit this good with generic Apple earbuds would be a damn shame, especially because designers are trying really hard to make headphones the next fashion accessory. Don’t let that go to waste.

Coach: These Skullcandy Grind On-Ear Headphones ($39.99) will make it look and feel like you’re riding first class even if you’re in the cheap(er) seats.

Business Class: Master & Dynamic MH40 Over-Ear Headphones ($399) don’t have the designer name attached to them like the next pair, but they’re equally gorgeous and are comfortable enough to wear for entire transatlantic flights.

First Class: If you really are standing in the priority seating line, don’t do anything less than the new Special Edition Studio Headphones from Alexander Wang and Beats ($600). The noise cancelling should prevent you from hearing the oohs and ahhs from the plebes still waiting to board.