1Mandy Moore, 2000
Getty ImagesAt 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.
2P!nk, 2000
Getty ImagesThe 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.
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3Gabrielle Union, 2000
Getty ImagesGabrielle def brought *it* in a pair of bedazzled white pants to the premiere of her movie Bring It On.
4Carmen Electra, 2000
Getty ImagesElectra matched her halter top to one of the many colors in her patchwork pants at the opening of the Maxim Motel in LA.
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5Will & Jada Pinkett Smith, 2000
Getty ImagesAt 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.
6Mariah Carey, 2000
GettyCarey 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.
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7Backstreet Boys, 2000
Getty ImagesNot one, but three, of the Backstreet Boys covered their necks with turtles for the Stockholm start of their Black & Blue tour.
8Eve, 2000
Getty ImagesUnable to choose between a flapper skirt and slashed leather pants, Eve wore both to the Source Hip-Hop Music Awards.
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9Gwyneth Paltrow, 2000
Getty ImagesAn 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.
10Reese Witherspoon, 2000
Brenda Chase//Getty ImagesReese 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.
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11Ming Na, 2000
Ron Galella//Getty ImagesMing 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.
12Taraji P. Henson, 2001
Ron Galella//Getty ImagesTaraji 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.
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13Brad Pitt and Jennifer Aniston, 2001
Vince Bucci//Getty ImagesThe purple leather jacket. The purple button-up. The bare midriff on Hollywood's girl next door. Show us something more early 2000s than this.
14Jennifer Lopez, 2001
Getty ImagesThis one was a practical look: J.Lo's sun-hat and thigh-high boots eliminated any need for SPF.
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15Gwen Stefani, 2001
Getty ImagesGwen 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.)
16Destiny's Child, 2001
Getty ImagesRemember when Beyoncé wasn’t allowed in public without wearing an outfit that matched her group members? Lol, how quaint.
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17Eva Longoria, 2001
Getty ImagesEva 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.
18Britney Spears & Justin Timberlake, 2001
Getty ImagesThe 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.
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19Kerry Washington, 2001
Getty ImagesWashington’s look for the premiere of Save the Last Dance included the interesting choice to accent black with both red and purple.
20Jessica Simpson, 2001
Getty ImagesIn 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.
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