Should We All Be Dressing Up for Flights Again?

When air travel was even more exclusive than it is today, circa 1950-1960, a fashionable crew known as the “Jet Set” took flying very seriously. Shows like Mad Men and The Marvelous Mrs. Maisel depict this golden age of travel, when women wore pillbox hats, men wore suit jackets, and tomato juice was the in-flight beverage of choice. I see traces of this era in my parents, whenever they head to the airport a little more dressed up than usual—my dad sports a watch, my mom her best pair of jeans—and it warms my heart (don’t even get me started on their printed-out plane tickets).

I’ve long believed we should go back to celebrating the feat that is air travel—I will not tolerate those who keep their window shades down, denying the wonders of the sky. Even though flying is much more common these days, that doesn’t make it any less special. I’m in favor of treating air travel as an event, if only because it’s much more fun to do so. Jon Hamm thinks so, too. But not everyone agrees. I polled a few frequent travelers to better understand where we stand on the return to decorum vis-a-vis the friendly skies.

Those in favor of dressing up to fly

“While I don’t think there’s any reason to return to a Mad Men-era approach to dressing for flights, I do think we’ve had enough advances in terms of technical/quasi-athletic fabrics in casual wear that you can do better than sweatpants and a raggedy old hoodie. There’s a whole category of ‘performance’ or wrinkle-free casual clothing now that’s comfortable but holds some kind of shape that helps you look more put together after a red-eye, like trousers that are actually elastic joggers, soft knit sweaters, or button-down shirts.” — Chantal Fernandez, Features Writer, The Cut

“Personally, whenever I leave the house I try to be very put-together and dressed well. That being said, with the prospect of an international flight ahead of me, wearing ultra casual attire and embracing the in-transit vibe is very tempting. Comfort over all else. But in some instances, I think it has gone too far. I don’t love a flight that feels…and looks like a slumber party. We certainly don’t have to dress formally on flights, but I’d love to see air travel somewhat elevated again. And caring for your outfit, even in the sky, can make the tedium of travel feel…and look better.” — Charles Gross, fashion and lifestyle influencer

“We should definitely bring back the art of ‘dressing up’ for flights. Comfort, utility, and warmth are essential, especially when you’re hurtling through the air in a metal tube, but that doesn’t mean you have to look like you just rolled out of bed. I’m not saying you have to dress like you’re walking the runway, but there’s something so elegant about showing a little style and effort. I personally love some tailored pants (with stretch!), and am not opposed to sweatpants, but chic joggers in luxe fabrics. Pair them with a structured jacket and fabulous scarf or wrap to stay cozy, a catch-all carry-on (I love the Carla Rockmore sling bag in a bold color), and don’t forget a pair of oversized sunglasses. Suddenly, you’re polished without sacrificing comfort. I love a look that says ‘effortless’ but still feels pulled together. So yes, let’s make flights fashionable again, but let’s not lose comfort in the process!” — Carla Rockmore, fashion designer and influencer

“I have to admit I don’t really understand some folks’ insistence that they dress in head-to-toe terry cloth on flights, particularly shorter flights. Air travel is a chance to be someone else for a few hours at a time. You’re unlikely to run into anyone you know and can lean into a slight air of mystery, so why not wear something enjoyable, fun, or even a bit bulky, to save space in your baggage? For me, that is very rarely sweats, though maybe the calculation is different for you. All of that said, I’m not a tiny person, so any discomfort I have on a flight usually has more to do with the ever-shrinking amount of legroom that I am squeezing my body into, so whether I’m wearing sweats or jeans doesn’t register so much to me.” — Joe Erbentraut, Editorial Director, Thrillist

Those against dressing up on flights

“Here’s the thing about the golden era of mid-century air travel: It wasn’t just the passengers who treated this as an event worth celebrating, it was the airlines too. They were welcoming, hospitable, and treated people like actual human beings who had parted with some share of their yearly income in exchange for a nice experience. This is, obviously, no longer the deal. Instead I am harried through a parade of humiliations before being cramped into what barely qualifies anymore as a proper seat. Put simply: Glamor cannot exist in the absence of dignity. If I am to be treated like a sack of potatoes then I may as well look like one.” — Brandy Jensen, Deputy Editor, Thrillist

“My thoughts on airplane attire can be summed up in one sentence, courtesy of Kim Cattrall: ‘I don’t want to be in a situation for even an hour where I’m not enjoying myself.’ As such, I cannot fathom putting on an underwire bra, no-stretch jeans, or (god forbid) high heels to do nothing but sit upright in a seat thousands of butts have assembled before me, where the only reason people are looking in my direction is because I happen to be in their line of sight on the way to the bathroom. I worry about enough leading up to a trip — that I squeeze every liquid I own into a measly 3.4 ounces, gather enough snacks should a Yellowjackets situation present itself, and remember to book the hotel before I arrive at my destination — that I can’t put ‘dressing up’ on that list. (Seriously: the pilot waving everyone off the plane at the end of the flight will not remember you.) In this economy, and especially if you’re sitting in economy, comfort is king. Give me stretchy joggers and a sweatshirt or give me nothing.” — Kelsey Castanon, Senior Content Director, PS

“Sometimes I ponder how fun it would be if we as a society collectively decided to start dressing up again—at the airport and in our everyday lives. But those daydreams are always interrupted by a harsh reality: Flying has become less and less enjoyable over the years, to the point where it seems passengers could die mid-flight and the airline wouldn’t refund the ticket. We are being packed like sardines, forced to pay extra for practically everything. Thus, I am in full support of being as comfortable as possible, whether that means wearing worn out pajamas, tacky athleisure, or a combination of the two. Plus, as someone with terrible flight anxiety, the last thing I need is to be wearing nice pants that dig into my ribcage or thinking about how shiny my hair looks.” — Kelsey Allen, Associate Editor, Thrillist

“I truly want to be someone who looks beautiful at the airport. I do. But—and this inhibits my fashion sense generally—comfort is paramount to me. I never want to feel the softness of my belly be pinched by unforgiving waistbands. I don’t want rigid denim to press and scrape into the seams of my thighs. This means that a fair number of great airport fits are immediately nixed. I try, of course. I’ve experimented with the trendy sweats and the flattering athleisure. I braid my hair, and try to keep my luggage neatly organized. But the end result is always the same: a grown woman clutching her “airport treats” (usually chicken nuggets and a seltzer), sweating as she treks across a terminal. I’m wearing a facemask and a hat, grumbling under my breath about security theater and the price of water, and imbued with a “frazzled woman” vibe the truly fashionable are never weighed down by. Most of the selfies I take in airports look like I am a shockingly old unaccompanied minor. It’s not glamorous, but at 28, it’s the best I’ve been able to manage so far. Maybe I’ll be hotter and cooler at the airport in my next few decades.” — Opheli Garcia Lawler, Senior Writer, Thrillist

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