Rapper/singer Lil Mama of “Lip Gloss” fame decided to get back in touch with her inner child (or rather — baby) with this infantile outfit she wore to the 2007 VMAs. We really have no idea why she decided to wear a puffy lilac satin dress with a matching baby bonnet.
To make things even stranger, she was photographed with a Swarovski crystal-encrusted pacifier which she actually proceeded to put in her mouth! While this outfit is a whole bunch of no, we do have to commend her on her sensible choice of shoe wear (an out-of-frame pair of bedazzled sneakers).
David Lee Roth, 1984
Compared to the outrageous antics former lead singer of the iconic band Van Halen has gotten up to in his career as a rock star, this tropical-inspired suit is actually pretty tame. In 1984, David Lee Roth took the concept of being on “island time” a bit too seriously when he showed up to the VMAs in this Hawaiian shirt-meets-suit and comical sunglasses.
In case his tropical flower-filled suit wasn't enough, the former-Van Halen frontman ditched the shirt and chose to wear several Hawaiian leis instead.
Amy Lee, 2003
In the early 2000s, Amy Lee brought a darker sound to the music industry as the lead vocalist of the rock band Evanescence. Though there’s no denying that Amy has an incredible set of pipes on her, her sense of style often left a lot to be desired.
In 2003 she wore this strange mismatched outfit to the MTV VMAs that left us all scratching our heads. Combining a gothic leather corset with a frilly skirt and those curls we all tried to make with a curling iron, Amy’s look hit a sour note with fashion critics!
Kacey Musgraves, 2021
If you’ve ever wondered what McDonald's Grimace would look like after a glamorous makeover, look no further than Kacey Musgraves’ 2021 VMAs dress.
The country singer decided to put a designer spin on the purple cartoon character’s trademark look with this deep purple Valentino Haute Couture dress topped with an oversized furry hat. In case that wasn’t enough purple, she also wore matching purple eyeshadow. While Kacey seemed happy about her choice, we’re sure that the audience members sitting behind her were less than appreciative.
Proving that she is actually a pop culture goddess, Cher strolled onto the red carpet wearing her famous sheer bodysuit from her iconic “If I Could Turn Back Time” music video. Though the video premiered in 1989, Cher looked equally amazing wearing an updated version of it in 2010!
While Cher’s Bob Mackie-designed jeweled bodystocking caused quite the commotion, she was easily outshined when she was joined on stage by Lady Gaga in a dress made out of actual meat! But the icon didn’t have any hard feelings about another style stealing the spotlight. In fact, she found it “hysterical”!