a man wearing a face mask

Some, are flirting for an upgrade. For others, it’s a different self, or in many cases, a more comfortable self. Airport fashion is my favorite of the fashions, largely because people step outside of their everyday, to become something else.

Sometimes, for the better and other times for the worse!

Partly for my own enjoyment, but also for the sake of an “amen”, I want to put my thoughts on the matter down on proverbial paper. Even the longest flight delays can often be passed with joy, thanks to the joys of people watching – and the never ending fashion show that comes with it.

Airport Fashion: A Reimagined Self

Our everyday lives can dictate our fashion choices, be it corporate policy or just keeping it basic and not drawing added attention. But I find that when people travel, they take things to a new gear. It probably started with the Hawaiian shirt.

People feel as if they’re on vacation time before they get there, which would also explain why many partake in slamming vodkas at 6AM. There’s simply no better place to people watch than an airport – other than perhaps a cougar bar.

After many years with too many flight delays, here’s how I think people break down their airport attire. Mainly, I think people feel comfortable to create a new persona with their airport fashion, transforming them into a psychological mindset.

a man wearing a face mask

The Upgrade Outfit

Any time major news outlets cover a topic with such voracity, people are going to play the game, particularly when added comfort is involved. There have been a series of nonsensical articles purporting that outfits can be the key to getting upgraded.

This can be the Gucci belt, the three piece suit, the power blouse or the Louis duffel, but I can’t think of any place (outside of the airport) where I see more designer logos proudly on display.

Do people feel free enough to peacock a little bit when they travel, or are they just angling for something? Either way, I love to watch it.

In my experience, if people are wearing a Gucci belt, they make sure they’re wearing a t-shirt short enough that the belt features. Whether that gets an upgrade or not, is for you to decide. My experience dictates that it does not, because I see an awful lot of designer gear walking past the forward cabin.

airport space
Cathay Pacific Lounge at HKG

The Comfy AF

Many travelers lament the “good ole days” when people wore suits, dresses and other formal wear to travel. I don’t. Seat dimensions have changed along with the prestige of air travel, and frankly, I can’t think of anything worse than being in a suit for 14 hours in economy.

Having said that, some of the levels people take “comfort” to, are hilarious. At times, it really can be hard to distinguish pajamas from comfortable clothes. Sometimes, there isn’t actually a need to distinguish, because they’re one in the same!

The “comfy AF” traveler also draws some parallels with the upgrade traveler, in a love for all things name brand. Hey, I totally get it – I love Commes De Garcons sweatshirts as much as the next.

I really struggle to knock this approach, mainly because air travel is largely a function of transport these days, and hardly some glorified comfortable means of getting around.

You do you, person wearing the full on track suit with shades on, hood up and comfortable slides, rather than actual shoes. Just wear socks, because bare feet are never ok on planes. Never!

The Letting Loose

This is honestly, probably where I fit in, but not always. Perhaps it’s an extra dash of color, or a little extra jazz, but I typically feel a bit looser when I travel, so I take some liberties, which I might not at home.

I adore – like, adore-adore – seeing people who go the extra mile with their Hawaiian shirts, or their “vacation time” t shirts. Travel is a celebration for most people, and a rare one at that. Seeing buttoned up people let loose, and send the universal signal for “i’m ready for a margarita” brings more joy than it does harm. Bless, you boomers!

This is the thrill of travel, and I’m often guilty of buying a new t-shirt, jeans, hoodie or something to travel in. There’s something exciting about getting away, and planning just a small statement to signify that for yourself can be lovely.

Above all though, function must meet and exceed fashion. This is comfort first, whether it’s the coziest leggings, as my partner loves, the softest cotton t-shirt or layers of feel good materials.

a person holding a suitcase

My Airport Fashion: Letting Loose, Comfortably

Above all, function must meet and exceed fashion. This can be interpreted a million different ways, but I think it’s an art form to look chic in a modern sense, while being entirely comfortable within yourself and your clothes.

Whether it’s the coziest leggings in the closest, which my partner loves for airports, or the softest cotton t-shirt or layers of feel good materials, I get it.

For me, I love hooded sweatshirts not only for the comfort and doubling as a pillow, but for keeping germs away – no joke – an epidemiologist told me how effective they can be! If it’s cold, I’ll layer a bomber jacket on top, but I’ll never say it on board!

I try to put my best ‘comfortable’ face forward when traveling, perhaps going for the stretch jeans rather than the drainpipes, and always prioritize shoes or sneakers with tremendous padding. I firmly believe upgrades are not decided by what you wear, and I prioritize securing upgrades by actual methods, so I can dress as I wish.

Say what you want about Kanye West, but Yeezy’s are incredibly comfortable to travel in. I’m also typically in Adidas Premier or On Running shoes, like their Cloud Edge.

A great joy of airport fashion also comes in discovery. I’m going to find new inspiration and ideas sitting at the boarding area in Tokyo. Those inspirations may slowly slip into my repertoire, and who knows – maybe something of mine into theirs.

There’s just nothing better than airport fashion and if your flight is delayed, a glass of wine and people watching might be just what the soul requires. Just perhaps not too many, because no one needs another flight diversion!

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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  1. This article made me smile so much! I love how you still find joy on people watching and travel in general. Traveling is a treat for most and we should savor every minute!

  2. I dress in accordance where I sit. First Class: best shoes and custom shirt, close shave. Business class: jeans, oxford shirt. Coach: who cares, no one else back there does. The primary reason I gave up on Southwest, stewardess earn their money on that airline. And then there is the quality of the air/small in Coach…………

  3. What’s the issue with feet? If I’m going on a package holiday somewhere hot, I often don’t take any proper shoes.

    I don’t put my bare feet on the floor, so I really don’t see the issue. It does seem to be something that Americans get upset about….

  4. Haha, great article! Thanks! 🙂 I wear comfortable clothes, especially for long flights. Stylish stretchy “suit” pants are the best thing that has happened since sliced bread.

  5. Flew a bit in the middle of the “Pandemic Armageddon” and was amazed by the extremes to which people went on both ends of the spectrum.
    Fascinating, because, we may not realize, but, sometimes, when we travel, we become caricatures of ourselves.

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