How to Dress for the Airport

LKC Aug 18 | 2023

Escaping to somewhere new is thrilling. Actually traveling anywhere is almost always a hassle. Even walking to the bodega or driving to the post office feels like a slog. So, when it’s a plane, train, or automobile, I have to steel my nerves before braving a trip anywhere.

Despite my aversion to the process of traveling, I’ve taken up the challenge and I’m actually pretty good at it. You grin, you bear it, and you master breezing through TSA until it’s second nature.

There are a few golden rules I follow whenever I go anywhere. From a 30-minute flight to a 30-hour sojourn, my rules are the same:

The first two tenets are pretty self-explanatory. But dressing for success takes a while to master. Airport style is the most chaotic fashion genre. Some people flaunt their pajamas. Some replicate those supermodel airport paparazzi from the 90s. It takes all kinds.

But is there truly a right way to dress for the airport? First, let’s put to bed the myth that dressing “smarter” will make your carrier more likely to upgrade you. I’ve seen people suffer through a flight wearing slacks and Sperrys to no avail. Spare yourself.

I say, dressing for success means dressing for both comfort and efficiency. I shiver to think of those people in the onesies trying to pee in an airport bathroom. Gross-gross-gross.

And since I launch straight into my itinerary the second I land — I never hit Paris without stopping at Wild & The Moon before I’ve even checked into my hotel — I want my airport look to seamlessly transition into my next activity.

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An intelligent airport outfit features pieces you can wear later in your trip. It shouldn’t just be restricted to arrival and departure. Mixing and matching are key. Repeat after me: nothing in your suitcase should live in a silo. Everything must have multiple uses.

Because life is a game of trial and error, I’ve made some brutal mistakes on my journey to virtuoso airport-style.

Mistake #1: Overpacking. You do not want to trail three suitcases along the bumpy, cobbled streets of European cities, let me tell you that. You don’t even want that burden in an airport. Now that I know better, I love being the person who breezes through security with one bag, laughs at baggage claim signs, and is in and out in minutes.

Mistake #2: Layering too many bulky clothing items. How many times have I imagined it was a bright idea to layer sweaters and jackets in the airport … just to be proven wrong. Sure, it saves a little room in your suitcase, but packing cubes go a long way. You’ll have to strip down in airport security. And you’ll probably be sweltering at your destination.

Mistake #3: Complicated shoes. Why are we surprised that we still have to remove our shoes at security? I pack only one pair of shoes in order to save space in my suitcase. And as for passing through security — I’ve learned to wear something easy to slip on and off.

With these tips — and more — under my belt (not that I’d ever wear a belt to the airport), I feel equipped to advise you on how to dress for airport success.

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The ultimate key is aiming for something in-between your typical loungewear and a vintage airport paparazzi shot Wear what makes you feel comfortable — even if it’s a worn-in pair of jeans — and whatever will help you zoom through the BS as fast as possible.

Godspeed.

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