Paris Hilton
That's hot! The Simple Life star was looking pretty in pink with a floral halter top, wrap skirt and matching baguette shoulder bag.
Justin Guarini and Kelly Clarkson
Then American Idol finalists, the two singing hopefuls were all-smiles in their Levi's outfits. Just six days after their VMAs appearance, Kelly won the first season of the music competition, while Justin was named runner-up.
Avril Lavigne
There's nothing complicated about the "Sk8er Boi" singer's outfit. After all, a tie and studded cuffs were wardrobe staples for the punk rocker at the time.
Gwen Stefani
The No Doubt frontwoman also channeled her inner rocker with studs.
Christina Aguilera
The pop star wasn't kidding when she sang about rocking tight hip huggers (low for sure) on "Dirrty." For her 2002 VMAs appearance, Xtina rocked a racy scarf top paired with a mini denim skirt.
Britney Spears
Oops... she did it again! The singer was clad head-to-toe in leather—albeit in black, as opposed to her iconic red catsuit—for her walk down the red carpet.
Pink
Pink was ready to get the party started with her temporary tattoo sleeve and side bangs.
Justin Timberlake
The boy bander may not be able to justify wearing a fuzzy hat, but the accessory was all the rage back in the early aughts.
Joey Fatone, JC Chasez and Chris Kirkpatrick
Who knew NSYNC was ready to say bye, bye, bye so soon? The 2002 VMAs marked one of the group's final red carpet appearances before splitting up later that year.
Jennifer Lopez
J.Lo was dressed to impress in a plunging blazer.
Kelly Osbourne
The Osbournes star played into the graphic tee trend with a top that read: "My Boyfriend Is Out of Town."
Enrique Iglesias and Anna Kournikova
There was no escaping this couple's romance during the early aughts. Enrique and Anna, who met on the set of the singer's "Escape" music video, started dating in 2001.
Kirsten Dunst
Fresh off the success of Spider-Man, the actress strutted her stuff in a military jacket and low-rise flared pants.
Michelle Branch
The dress-over-jeans trend was everywhere during the Y2K era. Case in point: Michelle's look at the 2002 VMAs.
Kate Hudson
The Almost Famous star also opted to pair her jeans with a dress.
Heath Ledger
The late 10 Things I Hate About You actor kept things smart-casual in a sports jacket and T-shirt.
Ashley and Mary-Kate Olsen
In true It-Girl fashion, the Full House alums were already tapping into the boho trend that was soon to make waves in the late aughts.