The Most Iconic '90s Outfits in VMAs History

While every decade has had its fair share of iconic looks at the MTV Video Music Awards, the '90s take the cake in my opinion. When else could you see Pamela Anderson in a gigantic pink hat, Destiny's Child in matching sherbert-hued looks, and Gwen Stefani in a furry bra?
Below, I rounded up my favorite '90s looks in VMAs history. Here's a hint of what to expect: The Spice Girls in their prime, Madonna in an elaborate costume for a performance, Jennifer Lopez in a sparkly top, and Cindy Crawford in a thoroughly modern outfit that could have been worn yesterday. Scroll down to revisit the most iconic looks from the MTV VMAs ahead of the 2025 event, which will be held on Sunday, September 7, in New York City.
Pamela Anderson, 1999
Carmen Electra, 1997
Lil Kim, 1999
Destiny's Child, 1998
Gwen Stefani, 1998
TLC, 1999
The Spice Girls, 1997
Cindy Crawford, 1993
Drew Barrymore, 1995
Madonna, 1990
Lenny Kravitz, 1993
MC Hammer, 1990
Jennifer Lopez, 1998

Erin got her start as aBest Knockoff Luxury Clothing intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.
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