bands/musicians The Most Outrageous Outfits Ever Worn to the MTV VMAs  

Jessica Lawshe
10.2k votes 981 voters 181.5k views 38 items

List Rules Vote for the most - OMG I can't believe they wore that - look

Just like MTV isn't really about music videos anymore, the VMAs aren't really about those moon man awards. They're about the fashion. Over the years, our fave celebs have really pulled out the stops. And let's just say that maybe some of them shouldn't have. Join us as we take a trip down memory nightmare lane and check out the crazy looks that make up our list of the most outrageous outfits ever worn to the MTV VMAs. 

The VMAs are all about the performances... on the red carpet. For years our fave artists have made some crazy VMA fashion choices. Sure, we could blame it on '90s fashion norms (*NSYNC, we're looking at you), but then it continued through the 2000s (Christina Aguilera, Fergie) and to modern times with Lady Gaga's infamous meat dress. 

We've documented some of the worst VMA fashion right here on our list, including Britney's rocker-chic look, and Lil' Kim's purple pasty. But let's be honest, these are ladies who could have been on this list multiple times. We also have to thank the VMAs for kicking off trends like "naked dresses" and "unicorn hair." You'll see who we're talking about there.

If you want to get inspired for your next big night out (or learn what mistakes to avoid), check out the most shocking VMA outfits. Vote for the most - OMG I can't believe they wore that - look!

Rose McGowan is listed (or ranked) 1 on the list The Most Outrageous Outfits Ever Worn to the MTV VMAs
Photo: via Tumblr
Rose McGowan kicked off the naked dress trend with this look in 1998. And you thought Marilyn Manson's outfit would have been more shocking.  see more on Rose McGowan

Britney Spears is listed (or ranked) 2 on the list The Most Outrageous Outfits Ever Worn to the MTV VMAs
Photo: via Tumblr
There are so many Britney options for this list (for example: her denim duo look with Justin Timberlake), but we decided her 2002 biker-chic look topped them all. 

Also Ranked

#29 on The Best Current Female Singers

#91 on The Greatest Former Child Stars

#67 on The Female Singer You Most Wish You Could Sound Like

#40 on The Most Iconic Celebrity First Names

see more on Britney Spears

Christina Aguilera is listed (or ranked) 3 on the list The Most Outrageous Outfits Ever Worn to the MTV VMAs
Photo: via Tumblr
Christina Aguilera was right in the middle of her "dirrty" phase when she wore this "outfit" to the 2002 VMAs. 

Also Ranked

#23 on The Best Singers of All Time

#6 on The Best Current Female Singers

#8 on The Best Female Vocalists Ever

#10 on The Greatest Singers of the Past 30 Years

see more on Christina Aguilera
4
203 255

Lil' Kim's Purple Pasty


Lil' Kim's Purple Past... is listed (or ranked) 4 on the list The Most Outrageous Outfits Ever Worn to the MTV VMAs
Photo: via Tumblr
L'il Kim wore the little pasty that shocked the world to the 1999 VMAs. More frightening was the moment when Diana Ross cupped it onstage.