Airport Style: Travel in Comfort

Airport Style: Travel in Comfort

Picture the tarmac in 1958.

The air smells like jet fuel and cigarette smoke, two scents that once meant glamour instead of headache. A woman crosses it in a tailored dress, white gloves buttoned at the wrist, a small hat pinned just so. A man beside her wears a three-piece suit and a fedora, sweating slightly in the sun, cigarette betwixt his fingers. They are not dressed up because it’s a private jet or an important occasion. They are dressed up because everyone on that airplane can afford to be there, and it is only appropriate that they do the same.

Now picture the security line in 2026.

Shoes off. Belt off. Laptop out. A man in joggers shuffles forward in socks, holding his pants up at the waist with one hand. A woman in a neck pillow, pajamas, and slides scrolls her phone while the line inches ahead. Nobody is dressed up. Nobody tries to be. A ticket that once cost a month's wages now costs an afternoon's work.

Somewhere between those two pictures is the whole story of how we got dressed to fly, and it says more about class, money, and comfort than it does about fashion.

The Golden Age: When Flying Was the Whole Event

Flying used to be expensive in a way that is hard to fully feel now. Aviation historian Guillaume de Syon of Albright College put it plainly to Fast Company: it was four to five times as expensive to fly during the Golden Age as it is today. A 1955 round-trip from Chicago to Phoenix on TWA ran $138, about $1,168 in today's money, and that same ticket in the 1950s could eat up to 5 percent of an entire year's salary. A transatlantic ticket in the early 1960s ran around $600, roughly $5,800 today. Flying was rare enough that by 1975, journalist George Will reported, about 80 percent of Americans had never once been on an airplane. Now nearly 90 percent have.

When something costs that much and so few people get to do it, you wear your good clothes. You dress the way you would for church, or a wedding, or dinner with someone you are trying to impress, because in a sense you are. Men wore suits and sober ties. Women wore dresses, heels, and pearls. As the 1960s loosened, a man might risk a flowery tie and a woman might add a fashionable scarf, hemlines climbing toward the mini as the decade wore on. Passengers posed for photos before boarding because the flight itself was the occasion, not an inconvenience wedged between two better things.

And the reward matched the effort. Seat pitch ran 36 to 40 inches, compared with 28 to 31 today. First class meant lobster and prime rib carved tableside on real china, Champagne poured into real glass, and on Pan Am's 747 a spiral staircase climbing to an upper-deck piano bar. Somebody had to name this life, and the columnist Igor Cassini, writing as "Cholly Knickerbocker," gave it one in the early 1950s: the jet set. His own brother Oleg Cassini dressed Jacqueline Kennedy. The glamour was a closed loop, and the airport was where it performed itself.

Pan Am: Selling a Lifestyle, Not a Seat

No airline built the fantasy better than Pan American World Airways. Founded in 1927 by Juan Trippe as a mail run between Key West and Havana, Pan Am became America's unofficial flag carrier, the first to circle the globe, the first to fly the Boeing 707 in 1958. The blue globe logo, the "Clipper" names on every aircraft, the white pilot caps: this was branding before branding had a name. Pan Am's own marketing claimed it epitomized the luxury of intercontinental travel, and for once, the marketing wasn't lying.

The stewardess was the brand made human, and the requirements were unforgiving. At least 5 feet 2, no more than 130 pounds with regular weigh-ins, single, no children, college preferred, fluent in at least one foreign language, mandatory retirement by 32. Most women lasted just 18 months in the job before the clock ran out on them. They wore girdles, white gloves in summer, black leather in winter, and always a hat. Real designers dressed them: Don Loper starting in 1959, then Frank Smith of Evan-Picone in 1969 with the "Uniform for the Superjet Era," offered in Superjet Blue or Galaxy Gold, complete with the airline's first above-the-knee hemline and a Borsalino bowler everyone called the Tally Ho.

Pan Am even planted a monument in Manhattan. The Pan Am Building, finished in 1963 above Grand Central Terminal, was the largest private office building in the world at the time. But the fall matched the rise for steepness. Juan Trippe retired in 1968 and died in 1981. Deregulation, a rocky acquisition, the 1988 Lockerbie bombing, and the 1991 Gulf War drained the company dry. On December 4, 1991, after 64 years, Pan Am simply stopped flying. A 2011 ABC series tried to bottle that 1963 glamour back up with Christina Ricci and Margot Robbie. It lasted 14 episodes.

TWA: Howard Hughes & a Terminal Shaped Like a Bird

Trans World Airlines was Pan Am's fiercest rival and, for a long stretch, Howard Hughes's personal obsession. Hughes bought control in 1939 and shaped the airline's identity down to the red-and-white paint job that outlasted every other decision he made. TWA dressed its crews in real couture across the decades: Howard Greer's 1940s "cutout" uniform, with openwork lettering and a flap you could unbutton to hide the logo while sneaking a cigarette off duty; Oleg Cassini starting in 1955; Valentino from 1971 to 1975 in muted plum and navy, paired, memorably, with a shirtdress worn over hot pants; then Stan Herman, and in 1978, Ralph Lauren.

But TWA's real masterpiece was a building, not a uniform. The TWA Flight Center at what is now JFK Airport was designed by Eero Saarinen and dedicated May 28, 1962. Its thin-shell concrete roof looked like a bird caught mid-takeoff, held up by four Y-shaped piers, and it became, in the words of one later critic, the world's most famous airport terminal. Saarinen died months before it opened and won a posthumous AIA Gold Medal for it. The terminal closed in 2001 when American Airlines absorbed TWA, then reopened in 2019 as the TWA Hotel, 512 rooms wrapped around Saarinen's original headhouse, with a cocktail lounge tucked inside a restored 1956 Lockheed Constellation and vintage hostess uniforms on display like the art they always were.

The Concorde: Faster Than the Sun, Dressed Accordingly

Then there was the Concorde, the needle-nosed Anglo-French dream that made every other plane in the sky look like it was standing still.

Born from a treaty Britain and France signed on November 29, 1962, it first flew on March 2, 1969, and entered commercial service January 21, 1976. It cruised at Mach 2.04, about 1,350 miles per hour, at 60,000 feet, high enough that passengers could see the curve of the Earth pressing against the black of space. British Airways put the math simply: a London-to-New York crossing took a little less than three and a half hours, versus about eight on a subsonic jet. The record run, in February 1996, clocked in at 2 hours, 52 minutes, 59 seconds. The airframe got so hot from friction it physically stretched, six to ten inches, every single flight.

This was the most exclusive cabin ever pressurized. A round-trip London-to-New York fare in the plane's final year ran roughly £6,600, with some estimates pushing the return ticket as high as £8,000 to £10,000, about ten times the cost of a business-class subsonic seat. The Queen Mother celebrated her 85th birthday aboard. Paul McCartney brought his guitar. Andy Warhol pocketed the long-stemmed cutlery, designed by Raymond Loewy, as a souvenir. British Airways dressed its cabin crew in Savile Row tailoring from Hardy Amies. One BA captain summed up the clientele as people of distinction in business, government, and the arts, who flew Concorde because they valued their time more than almost anything else money could buy.

The end came fast. Air France Flight 4590 crashed on July 25, 2000, killing 113 people. Combined with the post-9/11 travel slump and rising operating costs, the entire fleet was retired by 2003. Nothing has replaced it. Nothing has come close.

The Slow Unbuttoning: 1970s Into the 1980s

The loosening started quietly in the 1970s and became structural on October 24, 1978, when President Jimmy Carter signed the Airline Deregulation Act. Once the government stopped setting fares and routes, competition pushed prices down and passenger numbers up fast. By the Competitive Enterprise Institute's count, U.S. airline passenger volume rose 210 percent between 1978 and 2017, from about 250 million to roughly 850 million riders, while inflation-adjusted airfares fell more than 40 percent.

Historians will tell you to be careful about drawing a straight line from that law to what people wore. Aviation historian Janet Bednarek has pointed out that people stopped dressing for flights around the same time they stopped dressing for other everyday occasions, like a trip to the store, and calls the timing with deregulation coincidence rather than direct cause. The culture was already unbuttoning itself. Deregulation just handed everyone a ticket to be there when it happened.

The 1980s slowed the slide with sheer confidence. The power suit, the shoulder pads, the Brooks Brothers business traveler moving through the terminal like the terminal belonged to him. Flying was becoming a commute rather than an event, but it was still, for one more decade, a commute you dressed for.

1990s to Today: Comfort Wins, Then Everything Gets Complicated

By the 1990s and 2000s the transformation was complete. Athleisure, sweatpants, hoodies, flip-flops. The uniform of the skies became the uniform of the couch potato.

Then September 11, 2001 happened, the TSA was created, and the checkpoint turned into a ritual of removal that nobody could dress their way around. Before that day you could walk to the gate without a boarding pass, shoes still laced. After the 2001 shoe-bomber and the 2006 liquids plot, every traveler learned the same choreography: shoes off, belt off, jacket off, laptop out, liquids bagged.

Nobody understood this new reality better than Anthony Bourdain who spent his life logging a quarter million miles a year in pursuit of the next meal worth eating. His approach to the airport was ruthlessly, almost monastically practical. He told Main Line Today in 2011: "I pack for security, and it's all carry-on, shoes that slip on and off quickly, jackets that I can beat into submission, shirts that don't require pressing." He put it even more bluntly in a later New York Times interview on travel essentials: "Don't get angry. It doesn't help. Like a recidivist convict, you should go limp. Nothing else. And dress for security. I don't carry liquids or gels, I don't wear a belt or any jewelry, I get my stuff out and in the tray very quickly and I'm through." His shoe of choice was the Clarks Desert Boot, on and off in a second, and his pillow was a balled-up lightweight down jacket. Dress for the machine, not the mirror. That is, and should be, the entire modern philosophy of airline travel compressed into one breath.

However, this is not the case for recent times. 

People seem to dress like they’re sick teenagers or stay home from work after being in the hospital; donning pajamas and shower caps, showing off their toes in slides and flip flops, looking as if they haven’t showered for a week. It’s understandable that one wants to be comfortable for a long flight, but do not expect others to enjoy the company of your smelly feet if you take your shoes off on the plane. Or to express interest in interacting with you when you look like a slob in pajama bottoms and a ratty, old t-shirt. Self-respect is worth dressing well for, even if you’re not flying first class, but also to respect your neighbor. 

The Comeback: Dressing Well Again

Here is the good news. The pendulum is swinging back, and it does not require a girdle or tie to get on board.

A quiet-luxury sensibility has taken hold among travelers who refuse to pick between comfort and looking like they meant to leave the house. The formula is elevated basics: a cashmere sweater draped over the shoulders, wide-leg trousers, a camel coat for cooler routes, slip-on loafers built for the security line, a structured tote instead of a backpack, minimal mixed gold and silver jewelry, a neutral palette that reads as quiet money in motion. Fashion editors are saying the quiet part out loud now. Who What Wear argued in 2025 that stylish airport dressing is overdue for a comeback, with one writer flatly declaring she was making a case for bringing elevated airport style back.

Seventy years of airport fashion boils down to one lesson, and it is not that we should all go back to gloves and pillbox hats. It is that how you dress at the airport was never actually a fixed rule handed down from above. It moved with money, with security, with culture, and now it is moving again, back toward intention. You can slip your shoes off in the security line and still walk off the jet bridge looking like you belong somewhere better than economy class (even if you do fly economy).

So don’t wear the pajamas, or don the shower cap, or wear the slides, or show your dogs in flip flops, or wear the tank top. It doesn’t matter what class your ticket is in or section you board in. You can dress comfortably in style without the need for looking like a slob.

Dress for the trip you wish you were taking. Have respect for yourself and others, as somebody (eventually), always notices.

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