60 Celebrity Outfits From the Early 2000s That’ll Make You Say, “What a Different Time” (2024)

At a New York launch event for her album I Wanna Be with You, Mandy apparently wanted to be with a feather halter top and a knee-length denim skirt.

The singer attended the MTV VMAs sporting a cropped halter, floor-length fur coat, and jeans that maybe had earrings hanging on them? A bright-pink 'do also happened, naturally.

Gabrielle def brought *it* in a pair of bedazzled white pants to the premiere of her movie Bring It On.

Electra matched her halter top to one of the many colors in her patchwork pants at the opening of the Maxim Motel in LA.

At the Oscar De La Hoya Fight the World Welterweight Championship, Will was a bad boy in a red leather shirt, while Jada opted for a lower-back cut-out and a rhinestone decal.

Carey spread her wings at the VH1 Divas concert in a butterfly-shaped top paired with jeans that appeared to have had the waist sheared off.

Not one, but three, of the Backstreet Boys covered their necks with turtles for the Stockholm start of their Black & Blue tour.

Unable to choose between a flapper skirt and slashed leather pants, Eve wore both to the Source Hip-Hop Music Awards.

An absolute must of early ‘00s fashion: Always match your boots to your jacket, and don’t you dare forget to match your purse to your pants. Exhibit A: Gwyneth at the premiere of the movie The Next Best Thing.

Reese rocked not one, but two early 2000s trends at the Blockbuster Entertainment Awards (oof that's a throwback in itself): a strapless midi dress made out of a heavy crepe fabric.

Ming Na nailed a formal tonal look decades before it was trendy at the TV Guide Awards, but of course made sure to show off her midriff.

Taraji channeled the '60s in a paisley micro mini dress at the premiere of Rush Hour 2 and the 2000s sandal of choice: the heeled flip flop.

The purple leather jacket. The purple button-up. The bare midriff on Hollywood's girl next door. Show us something more early 2000s than this.

This one was a practical look: J.Lo's sun-hat and thigh-high boots eliminated any need for SPF.

Gwen Stefani rocked out in houndstooth gaucho pants, fishnets, and a red cutout top at the My VH1 Music Awards. No doubt, this was a win. (Apologies, had to.)

Remember when Beyoncé wasn’t allowed in public without wearing an outfit that matched her group members? Lol, how quaint.

Eva showed up to the Lara Croft: Tomb Raider premiere in patchwork leather pants in many shades of brown. The pants and the matching jacket made such a statement, no shirt was necessary.

The award for the most 2001-iest possible outfits goes to then-couple Britney and Justin, who popped up at the American Music Awards in head-to-toe denim.

Washington’s look for the premiere of Save the Last Dance included the interesting choice to accent black with both red and purple.

In case head-to-toe red pleather didn't make a bold enough statement at the American Music Awards, Jessica also included a rose detail at the bottom.