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”!
Lil Mama, 2007
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).
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.
Lil’ Kim, 2000
As the unofficial queen of outrageous outfits at the VMAs, Lil’ Kim did not disappoint with the plastic red outfit she wore to the 2000 awards show. Wearing a bustier romper made out of red transparent plastic, the “Lighters Up” rapper topped off her look with a matching bright red plastic jacket.
With all of those straps, studs, and sharp plastic edges, we just can’t imagine how uncomfortable this outfit must have been. On the bright side, with that PVC jacket, she was probably ready for any sort of rainy weather!
Missy Elliott, 2003
Missy Elliott may be one of the most talented artists in music, but even she couldn’t manage to “Work It” with this awful golf-inspired getup. Adidas tracksuits are already on most stylists’ no-no lists, so the fact that Missy chose to wear one in lime green and plaid probably enraged fashion critics even more.
In case the outfit couldn’t get worse, she topped it with this plaid hat and a huge yellow pom-pom. Why, Missy? Let’s hope she sent this terrible outfit to the big golf course in the sky!