23 Iconic Celebrity Airport Looks as Summer Travel Outfit Inspiration

Ah, the good old days, when you dressed up to fly, ordered your steak meal days before boarding, and could chain smoke the entire trip. That era may be long behind us, but there’s no reason why you can’t still get inspired by Marilyn Monroe’s airport look and don a skirt suit the next time you fly.

Similarly, Hepburn embraced the New Look on a flight to London in 1953. That extra-cinched waist might not be ideal for a long haul, but it sure looks chic.

A more comfortable option can be taken from the ’60s, when shift dresses ruled supreme.

All-leather might seem extreme in the summer, but you have to admit, Brigitte Bardot looks pretty great in her trench and over-the-knee boots. Good thing planes have air conditioning.

A more weather-appropriate option comes from Diana Ross in 1973—a simple look of bell-bottom pants and a white button-down, which can be easily spiced up with some statement accessories like a belt and necklace.

And if you don’t feel like engaging in color theory the morning of a big trip, opt for a monochrome look like Jackie O, made more interesting with a patterned blouse and some classic ’70s sunglasses.

By the ’80s, the days of dressing up for a flight were truly behind us. But inspiration can still come from more casual ensembles, like Whitney Houston’s oversize varsity jacket and rolled-up jeans.

Madonna’s leather moto jacket, ripped jeans, and loafers exemplified the cool factor of the decade. She wore this look at JFK in New York.

In the ’90s, all details and ornateness of the prior era were gone. Here, Kate Moss demonstrates the recipe for a perfect, simple airport look: a crisp white T, green cropped trousers, and animal print mules.

Layers are key when traveling, and Cindy Crawford proved in 1997 how to pull them off in a way that still looks stylish.

Jeans on an airplane might feel like a death sentence, but what about a denim skirt and crop top? That’s got to be more comfortable, right?

Of course, if comfort is your priority, you can always adopt the classic Paris Hilton aughts look of a velour Juicy Couture tracksuit.

Nicole Kidman proves one can look put-together while also prioritizing comfort. Plus, if you’re running to a meeting straight from the airport, you can easily throw a pair of heels into that capacious bag.

Of course, this is 2024, so pants are always an option for a flight. If jeans on the plane isn’t your thing, may we suggest camo cargo pants, à la Rihanna?

Or, embrace the tracksuit in a modern, fashionable way like Kendall Jenner in 2016.

Gwyneth Paltrow proved that a colorful sweater can enhance even the simplest look.

And while suiting is an undeniably smart way to dress for a trip, you don’t have to fully commit. Try pairing some oversize trousers with a more casual T, like Posh.

Of course, if you want to really embrace singular style at the airport, look no further than Chloë Sevigny, who often proves that individual taste should never be diminished by logistics.

Alternately, one great statement piece—like a suede fringe jacket—can add enough style to an otherwise comfy and casual look.

But if you really hate the idea of wearing anything on a plane that doesn’t feature an elastic waistband, consider Bella Hadid’s approach. This Jean Paul Gaultier set is very much the modern-day equivalent of Paris Hilton’s Juicy tracksuit.

Let’s not count out dresses: Elle Fanning looked incredibly chic when arriving to Cannes in 2022 wearing this caftan-adjacent garment. It was likely very comfortable on her long flight.

You can also top anything—even leggings—with a trench coat to completely transform the look.

And when in doubt, just wear all-black.