More of the Most Daring MTV VMA Fashion Looks of All Tim

By: Stephanie Feldman | Pulished on 2023-12-25

Gwen Stefani, 1998

We’re not exactly sure when it happened, but at some point during the late ‘90s, raver fashion moved from the underground to the red carpet. At least that’s what we think happened, otherwise, we really can’t explain Gwen Stefani’s look.

 

More of the Most Daring MTV VMA Fashion Looks of All Tim-Trip Advise

Getty Images Photo by Jeffrey Mayer

 

We’ve heard of matching accessories to your outfit, but most people don’t typically match their hair color to their bra! And that’s just what’s going on above the belt. Let’s not even get into her weirdly futuristic shiny skirt over pants. We’re really glad this chapter in Gwen's lookbook is done!

Lil’ Kim, 1999

There are few fashion moments as memorable as rapper Lil’ Kim wearing a lavender jumpsuit with just a seashell-shaped sequined pastie covering the other side of her chest.

 

More of the Most Daring MTV VMA Fashion Looks of All Tim-Trip Advise

Getty Images Photo by Ron Galella

 

The rapper came out to present the "Best Hip-Hop Video" award with icon Diana Ross. And in case her outfit wasn’t jaw-dropping enough, Ross actually outstretched her hand and gave her co-presenter a jiggle! Oh, and if you’re wondering just how that pastie stayed in place — her stylist used eyelash glue.

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