It’s vacation time, which means it’s time to consider what you’ll be wearing to survive airports, airplanes, layovers, and transportation – all while not looking like a slob. Modern air travel is largely a miserable experience, and it’s hard to resist the urge to do what you can to make yourself as comfortable as possible. Most of the people you see on airplanes and in airports will probably be wearing sweat pants or workout pants of some variety, and frankly, considering the tiny seats, flight delays, violent flight attendants, and lost baggage, I can’t fault them for that.

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Jacket

Pockets, pockets, pockets. Gum, chapstick, wallet, passport, boarding pass – all of these will have to go somewhere, and I absolutely hate carrying things in my hands through airports, because I’m certain I’ll drop something without noticing, or set something down and forget to pick it back up. Internal pockets are key, as is a cut comfortable enough to allow you to wear it all flight long or place luggage in the overhead bins.

• Ring Jacket AMJ07 – an ultra-light travel jacket from The Armoury
• Engineered Garments ‘Bedford’ from Context Clothing – a versatile jacket that’s perfect for traveling
• Grey suede Valstarino bomber from No Man Walks Alone – classic, stylish, comfortable…and a lot of pockets
• De Bonne Facture pilot jacket from Unionmade – classic style, lightweight comfort, impeccable quality
• Buzz Rickson’s M-65 from History Preservation – a classic, made to an incredible standard

 

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Shirt

There’s something about airports that makes everyone look like a slob. Things spill. Things wrinkle. If you’re the kind of guy who usually wears a crisp white tee and feels good, you’ll probably end up looking like you just rolled out of bed after a cheeto binge. A collar, or at least a button placket, keeps this effect at bay. Oh, and white is not a great shirt color choice – nothing stays clean on an airplane.

• Barena Henley from Mr. Porter – comfy, with enough a collar to keep you from looking like a scrub
• Evan Kinori lounge shirt – perfect over a tee, worn closed or open
• P. Johnson overshirt – a multi-pocketed, camp-collar shirt from Mr. Porter
• RRL knit linen overshirt – rollable sleeves, a lovely dye, and chest pockets make this a great pick
• Wings and Horns henley – cool enough to keep you looking good, comfy enough for a long day

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Pants

Yes, pants. If you opt for shorts, you run the risk of finding yourself freezing when the aircraft air-con kicks into hyperdrive. Additionally, I haven’t worn denim on a plane in years, and can safely say that even slim jeans are terrible airline pants. Instead, opt for a breathable, woven trouser of some kind (or at least a loose-cut twill) that will keep you comfortable when you’re sitting on the tarmac and the AC’s not on, as well as when you’re in the air and it’s blasting. As long as the cut is comfortable, the fabric shouldn’t matter that much – as long as it allows at least some airflow.

• Outlier injected linen pants – ultra-light, ultra-breathable, ultra-useful
• Carhartt WIP aviation pants from HBX – updated utility in a loose cut
• Universal Works fatigue pants from END – versatile and comfortable 
• Epaulet ‘Taylor’ trouser in navy hopsack – roomy where it counts, in a great summer fabric
• Yohji Yamamoto wide trousers from FWRD – embrace them, and you’ll reach for them all the time

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Shoes

Slip-on, slip-off. You know this, don’t you? Loafers, slip-on sneakers, or slippers are all good choices – shoes that you can remove and put on while the seatbelt sign is on are worth their weight in gold. Anyone who’s ever experienced the horrible feeling of trying to stuff swollen feet back into laced shoes or boots after a long flight knows how truly hellish an experience that is, so keep in mind that after hours in the air, even the walk to baggage claim is going to make your feet feel as tired and uncomfortable as if you’d been walking all day.

• Baudoin & Lange loafers in navy grey
• La Portegna travel slippers – ultra packable, perfect for stuffing in a bag
• Diemme suede slip-ons – a great variant on the classic slip-on from SSENSE
• Viberg chelsea boots from Blue Button Shop – if you’re going to wear boots, they might as well be slip-ons
• Edward Green Picadilly – perfect if you’re headed straight from the airport to a meeting