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Classic ’90s Airport Style To Have You Looking (and Feeling) Your Best While Flying

Classic ’90s Airport Style To Have You Looking (and Feeling) Your Best While Flying

Maybe I’m biased, but the ’90s stick out to me as one of the best eras of fashion. As the pendulum swung from ’80s excess and glamour, the ’90s were a little more subtle, offering a darker color palette and a looser all-around approach to style and tailoring.

Slowly but surely, the ’90s are creeping back into our wardrobe today. One instance is oversized pants, but it can be found elsewhere, too. Flannel shirts are back, as are grungier gear like Doc Martens and Converse. But if you really want to get inspired by what ’90s style looked like, look no further than what celebrities were wearing to and from the airport.

It’s a niche interest of mine to see how celebrities were dressing for travel, and the ’90s photos is a goldmine. Stars like Johnny Depp, Brad Pitt, and Michael Jordan showcased how casual streetwear somehow can feel and look more glamorous coming off the tarmac than off any movie set.

So, how do you achieve the perfect airport style? Well, it’s all in the basics.


The jacket needs to be oversized. That’s the most important thing. It needs to be big, bulky, and preferably vintage. It has to be big enough to hold up over your head to hide from the paparazzi and also look good draped over your arm while you juggle your coffee and a newspaper out of a taxi.

Devil-Dog Dungarees Denim Jacket

Devil-Dog Dungarees Denim Jacket

The Devil-Dog denim jacket is a great option that’s simply constructed and the perfect blue. Jean jackets are a classic that are endlessly adaptable to anyone’s wardrobe, making it one of those garments that’s easy to throw on and go. With something like this, go a size up for a comfortable look, as a denim jacket has a tendency to stay fitted and it’s all about keeping it loose-fitting here.

Buy Now $109

Carter Young Patchwork Oversized Bomber

Carter Young Patchwork Oversized Bomber

Using factory leftovers, Carter Young has created a patchwork jacket that looks second-hand but feels luxurious. With its oversized construction and muted brown color palette, it could easily be from the ’90s while still having a contemporary edge to it.

Buy Now $1,395


The ’90s were the gold rush for baseball caps. I don’t know why that is, but every single celebrity who threw one on looked ten times cooler. It’s just one of those articles of clothing that dresses down a look without taking anything away from the overall style of the outfit, making it easy to incorporate into anyone’s wardrobe.

Yankees '47 baseball cap

Yankees ‘47 Baseball Cap

As classic as they come and always the first on my list. I myself have worn a Yankees cap almost exclusively for two years and I’m not even a baseball fan. The Yankees cap (or, really, any baseball team) just adds that little bit of sportiness to your look that says you’re much too busy to pay attention to what you have on.

Buy Now $28

huckberry x coors banquet hat

Huckberry x Coors Banquet Hat

Huckberry’s Coors Banquet Hat takes the best elements of past decades and makes them feel contemporary. Looking like a hat your dad would have in the garage, the corduroy relaxes the overall feel and the classic Coors logo gives it a bit of cachet.

Buy Now $35


Even today, ’90s jeans are coveted on the second-hand market for their straight leg cut and slightly higher rise. While women have embraced this style of jean for some time, men now seem to be jumping on the bandwagon. Make sure to really go hard on the relaxed fit here, fellas, or your skinny jeans will make the proportions of the ’90s airport outfit feel out of whack.

Levis 501

Levi’s 501

Is there any pair of jeans more famous than the 501? Levi’s mainstay cut, the 501’s straight leg gave Seinfeld his signature look and donned many celebrities of that day, like George Clooney and Brad Pitt, to name a few. It’s just as popular today and for good reason: it’s a style that, well, never goes out of style. Opt for a light wash for that real ’90s look.

Buy Now $98

Abercrombie and Fitch loose jeans

Abercrombie & Fitch Loose Jeans

If you’re looking for an alternative to Levi’s, A&F has really upped the game lately. With a generous cut and a variety of color options, it has some flexibility for those who want that ’90s relaxed feel without breaking the bank.

Buy Now $79


If you’re looking to keep the sun (or paparazzi’s flashing cameras) out of your eyes, you’ll want a pair of sunglasses that can do the hard work for you. I say stick with the classic here or you’ll fall into the trap of buying something too trendy. If you want to go retro, you have to commit.

Ran Ban Aviators

Ray-Ban Aviators

An oversized pair of sunglasses are a great way to look cool without adding too much else to your wardrobe. No one makes them better than Ray-Ban, who has perfected the design over the last century. Keep it classic with brown lenses and a gold frame and they’ll never go out of style.

Buy Now $163+

Persol 649

Persol 649

If you want to go less American and more European, grab a pair of Persol 649. A favorite of Italian movie stars and Hollywood producers, the 649’s oversized shape and keyhole nose bridge makes them exceptionally comfortable to wear for long periods of time and look great while doing so.

Buy Now $279