Twenty years ago—as millennium festivities kicked off around the world—the year’s most fashionable icons hit red carpets in quintessential ‘90s garb. Baggy jeans, biker jackets and retro windbreakers (yes, we remember) ruled streetwear, and runway designs reflected those looser silhouettes.
Many of the celebs dominating the fashion scene today have had remarkable careers spanning 20 years or more. Their looks, just like their careers, have evolved with age. But as the saying goes, history repeats itself—and ‘90s fashion has made somewhat of a resurgence (hello, tracksuits and platform shoes). Some looks may never come back—frosted tips, we’ll see you... maybe never—but others have stood the test of time.
Today's red carpet icons adopted some of the heyday's trendiest fits while others forged their own unique style path. Take a look at what your favorite celebs wore in 1999 versus what they’re wearing now in 2019.