Smell that? TSA checkpoints across the United States are free of their signature aroma for the first time in over two decades. On July 8, 2025, the Department of Homeland Security lifted the 19-year-long shoe-removal rule at airport security, ending an era of socks and bare feet shuffling across busy terminal floors. It’s a small policy change with heavy cultural weight: with shoes staying on, intentional dressing at the airport may be back on the table.
Trend forecaster Mandy Lee’s (also known online as @oldloserinbrooklyn) airport shoe of choice this fashion month? Nike Air Rifts, the split-toe sneaker-Mary Janes that have quietly surged in popularity this year, thanks to TikTok. “They’re easy to slip on, stylish enough to dress up, and comfortable for an entire flight,” Lee explains. If more elevated footwear makes it through the gate, might the rest of the outfit follow? The real question is not whether airport style can return to ‘50s and ‘60s glamour, but if it can mesh with post-9/11 practicality.
From 1955 through the early 1970s, during a period dubbed “The Jet Age,” the clothes you wore to the airport were synonymous with occasionwear, chosen with the same sense of importance. The occasion? The flight itself. Pumps, suit sets tailored to perfection, and dramatic fur stoles lined the aisles of flights long and short. “Airports were definitely looking into luxury, cutting-edge architecture, and signaling that idea of progress and modern advancement,” says Summer Anne Lee, a fashion historian and adjunct instructor at the Fashion Institute of Technology. On airplanes, space and comfort grew, but so did airfare, making air travel itself the ultimate flex. Airplanes were even the backdrop in glossy editorials, like the July 1957 and January 1962 issues of Vogue, further cementing the image of air travel as undeniably fashionable and aspirational. It’s important to note that mid-century fashion was anything but casual comfort. “People got more dressed up to leave the house in general then,” explains Lee. “So while they might not wear a fur stole to the corner store, men were still wearing suits and ties to baseball games.”
Even Don Draper ends up in jeans and a white tee by the Mad Men series finale. The formality of the 1950s and ‘60s unraveled in two waves–first, the casual turn of the 1970s. “There was more democratization of air travel in the ‘70s because airlines were encouraged to adopt competitive pricing,” Lee says. Flying became less exclusive, and therefore less aspirational. Meanwhile, fashion itself was loosening its metaphorical tie. Levi s and other denim became everyday staples, as men traded suits for knitwear and women increasingly wore trousers and adopted menswear elements to their looks, à la Diane Keaton.
The second wave came later as US airport policies shifted following the attacks on September 11, 2001. “After 9/11, you had to partially undress to go through security,” Jonathan Square, assistant professor of Black Visual Culture at Parsons School of Design, says. Later, in 2006, TSA implemented the “shoes off” policy in response to an attempted 2001 terrorist attack where a man tried to detonate bombs hidden in his shoes. Consequently, safety became the top priority for travelers, leading to a more pragmatic approach to airport dressing. What was once about projecting status became about surviving the process. “You’re not going to wear Rick Owens Kiss boots or Marc Jacobs Kiki boots, you’re going to wear something you can easily slip off and on,” Square adds.
Despite beefed-up security measures in the years since 9/11, airport fashion has remained culturally significant. Throughout the 1990s and early 2000s, celebrities perfected the intentionally casual yet unmistakably performative “airport look.” Paparazzi swarmed the scene at baggage claim to score a shot of celebrities like Kate Moss or Mary-Kate and Ashley Olsen, fresh off their flight. Celebrity stylist Micaela Erlanger points to her favorite moment–Victoria Beckham stepping off a plane in stilettos and a body-con dress in 2007. “In the early 2000s, celebrities were still dressing for the paparazzi–think oversized sunglasses, heels, and ‘It’ bags,” she says. Unlike Posh, most celebrities and everyday travelers took a much more casual approach. “Then came the rise of athleisure, wellness culture, and more security policies, which demanded shoes you could slip on and off, wrinkle-proof fabrics, and layers you could shed quickly,” Erlanger adds.
Airport ’fits–then and now–has largely been about curating one’s image. These days, even the bins at security are getting the curatorial treatment. But while the front-facing camera of travel is increasingly curated, the infrastructure hasn’t caught up–seats are shrinking, lines are longer, and space feels tighter than ever, leaving everyday travelers little choice but to dress down. “Because the flying experience has become more uncomfortable, people are searching for ways to deal with it. That means people are less concerned about how they look when they re flying, and more concerned about simply staying comfortable while doing it,” says Julian Kheel, CEO and founder of Points Path, a travel-related Google Chrome extension, noting that some airlines even hand out pajamas on long-haul flights. “The fact that society has deemed it acceptable to sit in a first-class seat wearing less than first-class clothes makes it hard to want to dress up for your flight.”
Decades ago, passengers could light a cigarette in the cabin. Chances are that’s not coming back–and neither is dressing up to fly, according to Expedia travel expert Melanie Fish. “It’s up to us to make smaller cabins packed with more seats as comfortable as possible,” she suggests. “And that’s hard to do in anything but stretchy fabrics and sneakers.”
Which brings us to the present moment, where travelers want the best of both worlds. The discomfort of flying still demands stretch and comfort, but the rise of social media and curated travel moments has reignited a desire to look put-together–even in coach. Younger travelers yearn for the elegance of yesteryear while remaining practical, aiming for a hybrid between the two. Trend forecaster Maggie Klimuszko frames it as a shift away from the sweatpants stretch of the pandemic: “The days of grabbing a morning matcha in your sweat set are dwindling. People want to feel polished and sophisticated when they’re traveling, but they’re not willing to sacrifice comfort or ease,” she says. The look is less pencil skirt, more trouser-and-sweater set. When asked how she sees airport fashion evolving in the next two to three years, Klimuszko predicts a traveler who is “comfortable, but also put together.” Think a coordinated luggage set, a massive oversized tote straight off the runway, and silhouettes rooted in timeless classics. “I think they are in a Canadian tuxedo–denim on denim with maybe a red knit sweater. I think a loafer, a kitten heel, maybe, definitely a chic boot,” she says.
But as Lee notes, there’s also a countercurrent: the return of sacrificing comfort for style. She predicts that the cultural rightward shift could bring back an appetite for discomfort–like the rise of everyday high heels–even if it means limping through an airport concourse and packing extra Band-Aids in your carry-on. “I really think it’s a natural progression of conservatism’s influence on the industry: an increase in suffering, essentially,” she says. Taken together, the two perspectives suggest that the future of airport style may hinge on how much discomfort people are once again willing to accept in the name of fashion.
For buyers, editors, and other industry folk shuttling between cities during fashion month, airport outfits come down to quick decisions. For stylists, the airport isn’t just a stopover on the job. “There was a time I flew straight to Paris, dropped my bags at the hotel, got a client ready, and ended up at a dinner under the Eiffel Tower all within two hours,” recalls stylist Lauren Jeworski. “You have to be prepared for comfort on the flight but still ready to transition quickly once you land.”
Nearly 25 years of bare feet on cold airport floors may have stripped flying of its glitz and glam, but the return of shoes staying on at security checkpoints suggests something larger: the opportunity to fully commit to your look when traveling. You never know, your outfit could take you places.