Jennifer Aniston's 1999 Airport Outfit Is Ripe for Copying

In the late ’90s, no one mastered effortless style quite like Jennifer Aniston. One of her airport outfits from 1999, in particular, is still inspiring the chicest flyers in 2025. The look was disarmingly simple—a crisp white tee, a long gray cardigan, classic chino pants, and black clogs—but that’s exactly what made it timeless. I’ve always believed the best travel outfits strike the balance between cozy and pulled together, and Aniston’s formula still nails it decades later. Maybe it’s nostalgia or perhaps it’s the fact that most of us want to look presentable when we’re speed-walking to our gate, but this outfit continues to resonate. Every time I see a traveler wearing some version of it at airports in Los Angeles, Copenhagen, Paris, and New York, I can’t help but think Jen was ahead of her time.

That’s the energy I wanted to capture with this story: unfussy pieces that feel as current today as they did when Friends was still on the air. The renewed popularity of clogs certainly helps. And a long cardigan? It’s essentially a wearable blanket that also makes you look like you have your life together. When you combine those elements with chinos and a white tee, you get a travel uniform that works in any decade. Below, I’ve rounded up updated versions of each piece so you can channel Aniston’s iconic airport aesthetic.

(Image credit: Shutterstock)