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Most Memorable Celebrity Fashion Fails

#1/16:

Madonna

#1/16:

Madonna

We’ve always been a little intimidated by Madonna – her cone boobs, her scary-lean biceps, and her sharp tongue, but the ’09 Costume Institute Gala was the first time her hair made us take a step back.
#2/16:

Snooki

#2/16:

Snooki

Oh Snooks, it’s true: we love to hate. But you keep making it so dang easy. We’re proud of you for slimming down to a size four, but still… put that cover-up back on.
#3/16:

Deena Cortese

#3/16:

Deena Cortese

Jersey Shore's Deena Nicole Cortese might be a "blast in a glass," but this buns-baring getup is worse than the trash on the Jersey Turnpike.
#4/16:

Lady Gaga

#4/16:

Lady Gaga

We’re usually all for Gaga’s self-expression, but Gaga’s meat dress from the 2010 MTV VMAs takes the (beef) cake. We can’t help but imagine the smell after something like that, so we just had to include her, little monsters. Forgive us.
#5/16:

Bjork

#5/16:

Bjork

We’d be amiss if we left Bjork out of this bracket since, after all, she’s been working up to this moment her entire career.
#6/16:

Britney Spears

#6/16:

Britney Spears

In Brit Brit’s defense, it’s tough to keep up with your root coloring and long hair extensions when you’re in bat-sh#t-crazy mode.
#8/16:

Janet Jackson

#8/16:

Janet Jackson

Jackson’s iconic Super Bowl wardrobe malfunction made us all wonder, what’s worse: nipple clamps or nip slips? Half-time shows will never be the same!
#10/16:

Lindsay Lohan

#10/16:

Lindsay Lohan

Just when we thought we’d seen enough of Lohan’s lady parts, she so graciously shared her side boob in this cutoff t-shirt. We'd actually rather see your brown chompers, Linds.
#11/16:

Mischa Barton

#11/16:

Mischa Barton

We’re not sure where to begin here, but we’ll start by admitting that we just didn’t know how hard life really was for the out-of-work actress. Good news for Mischa, though – new Goodwill’s are popping up nationwide.
#12/16:

Monique

#12/16:

Monique

"I must show America what a real leg looks like . . . because it's too much in the morning, every morning, to shave, to cut, you got Band-aids baby," MoNique once told Barbara Walters. Give us a bweak.
#13/16:

Nicole Kidman

#13/16:

Nicole Kidman

How could we forget when Kidman arrived to the premiere of Nine so unaware that she was suffering from this powdery make-up malfunction.
#14/16:

Sofia Vergara

#14/16:

Sofia Vergara

Sofia Vergara takes that "sexiest woman ever" thing way a little too far with her see-through yoga pants, but we’re willing to bet that her workout studio has a whole new list of sign-ups now.
#15/16:

Tara Reid

#15/16:

Tara Reid

After Tara showed off her butcher job at a party in NYC, Joey Fatone was wearing her boobs on a joke shirt a day later. We're not sure what's worse: Having Joey Fatone make fun of you, or acting in the movie Senior Skip Day. We'll go with Fatone.
#16/16:

Taylor Momsen

#16/16:

Taylor Momsen

Former Gossip Girl star Taylor No-Pants Momsen has a lot of #whitegirlproblems – it's really hard to live in a posh mansion on the Upper East Side when all you want to do is dress like a sewer rat. We get that she's a rebel and all, but she can at least wear pants. No one ever died of a shower and a pair of jeans.
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