The 20 most outrageous Grammy dresses of all time
Lady Gaga, 2011 Grammys
Lady Gaga may not have worn an outfit exactly, but her egg entrance was certainly outrageous. To be fully prepared for her performance at the Grammys, the superstar felt she needed to “incubate” before the show (yes, that’s Gaga inside the egg!). But let’s be honest—if she had shown up in an elegant column dress, we would have been disappointed.
M.I.A., 2009 Grammys
M.I.A. arrived to the Grammys red carpet very pregnant…the show was on her due date! The “Paper Planes” rapper wasn’t about to let her impending labor take away from her risky style, though, so she wore this colorful printed look, complete with high-tops for maximum comfort.
Cyndi Lauper, 1984 Grammys
The Technicolor hair. The fruit necklace. The shoulder pads. Cyndi Lauper gives us the best of the ’80s in this eclectic ensemble, and we have to hand it to her—she looks like she’s having a blast!
Cher, 2008 Grammys
Leave it to Cher to wear the biggest, most commanding dress in the house. The living legend chose this ruched, distressed, sheer ball gown for her Grammy appearance, proving once again that she’s one of the ballsiest ladies in the biz.
Jennifer Lopez, 2000 Grammys
You could say J.Lo is responsible for kick-starting the big ultra-deep V trend. We’re still talking about her tropical Versace dress with the below-the-bellybutton “neckline.” One thing’s for sure: She worked it.
Destiny’s Child, 2001 Grammys
Before Beyoncé was Beyoncé, she wore this spangled, Poison Ivy-esque dress to the Grammys when she was in Destiny’s Child (along with Kelly Rowland and Michelle Williams). Whether you prefer the jumpsuit version, the mermaid dress or the bikini-top/sari combo, there’s a look for everyone.
Sinead O’Connor, 1989 Grammys
Back in the day, Sinead O’ Connor was just your average outspoken singer-songwriter with a shaved head. Between the cropped moto jacket, graphic T and patched jeans (anyone else dying to know who this “Jake” is?), Sinead cemented her status as music’s rebel chick with a cause with this Grammy look.
Missy Elliott, 2002 Grammys
The “Work It” rapper showed some serious guts wearing purple leather from head to toe, complete with bell-sleeves and -bottoms (Elvis would be proud!). She went for a lot of look, but if anyone can pull it off, Missy Elliott can.
Madonna, 1999 Grammys
We all know Madonna loves to make a splash, and the Grammys are the perfect event to do so. This bold kimono-inspired look was from her “Frozen” phase (remember that video?), and she owned it, Coca-Cola and all.
Rihanna, 2011 Grammys
Only Rihanna could make this white ruffled, see-through extravaganza of a dress chic instead of silly. We’re huge fans of the “We Found Love” singer’s daring style, and from her confident Grammy pose, we’re guessing she loves her look too.