The Wildest and Most Memorable Looks From the Early 2000s: Jennifer Lopez, Ashley Tisdale and More

Let’s be honest: the early 2000s was a bit like the wild wild west when it came to fashion. Some of the most iconic — and questionable — outfits were born of that decade.

When Jennifer Lopez attended the 42nd Grammy Awards in 2000, her plunging green jungle-print dress made headlines around the world — and led to the launch of Google images.

At the American Music Awards the following year, Britney Spears and Justin Timberlake cemented themselves in the Y2K style hall of fame when they wore matching denim-on-denim outfits .

Flash forward to the mid-2000s, during Disney Channel’s heyday, stars like Ashley Tisdale and Miley Cryus inspired us all to embrace the power of layers — whether that meant wearing a tunic over jeans, a t-shirt over a tank top or a skirt over pants.

Whichever Y2K fashion moment you care to point to, they all shared one undeniable trait: none of them were boring.

Keep scrolling to see these looks and more.