The airport serves a primary purpose: getting you from point A to point B. And, if we’re being honest, there’s rarely anything glamorous about the experience. Still, that didn’t stop celebrities in the 2000s from treating terminals like their personal runways. Sure, ’90s airport style gets plenty of praise—thanks in no small part to supermodels like Cindy Crawford and Kate Moss, who mastered the art of effortless, unfussy travel style—but the decade that followed delivered just as many memorable looks.

But why was airport fashion such a thing during this era? For one, paparazzi culture was at its peak in the 2000s, with photographers routinely camping out at major airports like LAX and JFK. These candid arrivals and departures offered a rare glimpse at celebrities off duty, rather than all dolled up for the red carpet. Perhaps that’s why the era’s airport style was so appealing: The outfits rarely looked overly styled. In fact, many seemed as though they’d been thrown together minutes before heading out the door—which, of course, was all part of the charm.