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

Pamela Anderson, 1999

Let’s be honest; subtlety is not a word in Pamela Anderson’s vocabulary. Like most things on the buxom blonde, Pamela also prefers her hats supersized. The centerfold applied the “bigger is better” to her headgear.

 

Getty Images Photo by Kevin.Mazur

 

The Baywatch babe turned to celebrity milliner, hat designer Ivy Supersonic, to create the oversized pink hat she wore to the 1999 VMAs. Pamela paired the huge pink feathered hat with a skin-tight white corset, bedazzled sequin pants, and heavy eye makeup. With then-husband rocker Tommy Lee, her look epitomized the style of the late ‘90s.

Macy Gray, 2001

Before social media, artists had to get creative when it came to promoting their new projects. And what better place to share what you’re working on than the VMAs? Singer Macy Gray decided to use her body as a walking billboard when she ironed letters that spelled out the words “MY NEW ALBUM DROPS SEPT. 18 2001” onto her dress.

 

Getty Images Photo by KMazur

 

In case that was too subtle, the back was emblazoned with the command, “BUY IT.” Geez, Macy, we get it! Unfortunately, her little PR arts and crafts projects didn’t really work, and the album flopped.