Cher, Oscars 1986
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She's got some rockin' abs and props to her for showing them off, but we feel pretty bad for whoever had to sit behind Cher at the Academy Awards that year.
Photo: Jim Smeal/WireImage/Getty
Demi Moore, Oscars 1989
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This dress had potential (if you could even call it a dress), but we just can't get over those bermuda-length shorts underneath. She looks like she's about to hop on a bike and join the cyclists in Rio.
Photo: Jim Smeal/WireImage/Getty
Geena Davis, Oscars 1992
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With this getup, Geena has topped countless lists as one of the worst Oscars dresses ever—and it's not very difficult to see why. She looks like a Disney princess who lost the front of her gown.
Photo: Ron Galella/WireImage/Getty
Whoopi Goldberg, Oscars 1993
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Did Whoopi Goldberg buy this costume from a Halloween store? Or maybe it's a one-of-a-kind ensemble designed by Barney himself?
Photo: Kevin Mazur/WireImage/Getty
Lizzy Gardiner, Oscars 1995
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Lizzy Gardiner is an Australian costume designer, so when the 1995 Oscars rolled around, she decided to design her very own dress made entirely of American Express gold cards. The ironic part is that she won an Oscar for Best Costume Designer that year.
Photo: Photo by KMazur/WireImage/Getty
Lil' Kim, MTV VMA's 1999
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Who could forget rapper Lil' Kim's purple pasty at the 1999 Video Music Awards? She famously bared a single breast with nothing but a bejeweled sticker covering her nipple. Miley Cyrus recreated the look years later for Halloween in 2013.
Photo: Vinnie Zuffante/Getty Images
Celine Dion, Oscars 1999
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This may just be one of the worst fashion faux paus we've ever seen. Who in the hell told Celine Dion that it was a good idea to wear a pantsuit backwards? With sunglasses and a matching fedora? She looks like Kriss Kross and the Backstreet Boys rolled into one giant mess.
Photo: Jeffrey Mayer/WireImage/Getty
Jennifer Lopez, Grammy Awards 2000
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We're all about the deep-V trend, but JLo took it a little too far (like, past-her-bellybutton far). While we love how fearless and confident the singer can be, we're not so sure we love this outfit choice. Luckily, JLo recently recreated the Versace look, and she definitely wore it better this time around.
Photo: S. Granitz/WireImage/Getty
Tyra Banks, Oscars 2000
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Tyra, were you on your way to the Academy Awards, or the senior prom? This poufy lavender frock reminds us of something Tyra's Barbie character, Eve, would wear in the Disney movie Life-Size.
Photo: Steve Granitz/WireImage/Getty
Pamela Anderson, Oscars 2001
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If you can't find anything nice to say, don't say anything at all... but we HAVE to say something. Pamela, this is the Academy Awards, not an audition to be in a Britney Spears' music video. Too many nip-slips to count. And does her necklace say "PIMP"? *cringe*
Photo: Evan Agostini/Getty Images
Christina Aguilera, Blockbuster Entertainment Awards 2001
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We love you, Xtina, but what in the world were you thinking? This extremely ribbed dress reminds us of Gaga's meat ensemble at the 2010 VMA's. With the huge afro and gaudy accessories, Christina's look is way too over-the-top.
Photo: SGranitz/Getty images
Bjork, Oscars 2001
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Perhaps the biggest ridicule of the Oscars red carpet is Bjork's infamous swan dress of 2001. Bjork even told GQ that she "laid eggs" all over the Oscars red carpet, but other bodyguards kept picking them up thinking she dropped something. The dress, despite the criticism it received, found a home at the Museum of Modern Art in NYC (because TBH it was meant to hang in a museum and not on someone's body).
Photo: Jeffrey Mayer/WireImage/Getty
Jennifer Connelly, Oscars 2002
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Is this really the only outfit she could come up with to WIN an Oscar in? That shape doesn't flatter her whatsoever, the bottom looks like it was attacked by wolves, and don't even get us started on the mismatched scarf. Jennifer has definitely had better moments.
Photo: Frank Trapper/Getty Images
Hilary Swank, Oscars 2003
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We think Hilary looked 10X better as badass Maggie Fitzgerald in Million Dollar Baby. This dress makes her look like a tween on her way to the homecoming dance.
Photo: SGranitz/Getty Images
Paris Hilton, MTV Movie Awards 2003
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Paris, girl, we're about two inches away from seeing your va-jay-jay. She's always been a fan of showing off her toned midriff, but this outfit isn't exactly doing her any favors. And neither are her middle-school diva poses (pictured with little sis, Nicky, who ironically looks far more mature than Paris).
Photo: Dave Hogan/Getty Images
Nicole Richie, Teen Vogue Young Hollywood Party 2003
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Paris' ex-BFF Nicole also made our list with this dress that looks more like a shirt. And even if it were a shirt, it'd be a pretty ugly shirt.
Photo: Amanda Edwards/Getty Images
Uma Thurman, Oscars 2004
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Us: Uma, what's your secret?
UT: Well I was running late, so I just yanked some old curtains off of my windows and wrapped them around myself.
Us: Seems legit.
Photo: Frazer Harrison/Getty Images
Faye Dunaway, Oscars 2007
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The neckline. The sleeves. The RUFFLES. Make that two tiers of ruffles, actually. This dress is simply in no way flattering.
Photo: HECTOR MATA/AFP/Getty Images
Tilda Swinton, Oscars 2009
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For a split second, we thought she wasn't wearing anything on top. Then we realized her dress blended into her skin. This is a definite Oscar DON'T.
Photo: Frank Trapper/Corbis via Getty Images
Lady Gaga, BRIT awards 2010
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We can't forget to include Lady G in on the fun. Of all the crazy outfits she's donned over the years, this red-carpet getup really freaks us out. The piles of hair combined with the odd-looking dress earns her a spot on the list.
Photo: Mike Marsland/Getty Images
Nicki Minaj, MTV VMA's 2011
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There are so many wild Nicki Minaj looks, it was hard to narrow them down. That is, until we saw this one—by far one of the most outrageous red carpet ensembles ever. Three words: What. Is. Happening?
Photo: Steve Granitz/Getty Images
Kim Kardashian, MET Gala 2013
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Kim caught lots of flack for wearing this flowery turtle-necked disaster. Even Kim's own sister, Khloé, agreed that the head-to-toe pattern (including gloves) was not flattering. Twitter users had fun comparing Kim to Mrs. Doubtfire, Homer Simpson, and—wait for it—a couch.
Photo: Larry Busacca/Getty Images
Miley Cyrus, iHeartRadio Music Festival 2013
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Everybody makes mistakes, everybody has those days. And for Miley, that day was the iHeartRadio Music Festival in 2013. Back at it again with the pasties. It looks like she took her entire outfit and put it on her arms.
Photo: RD/Kabik/Retna Digital/Corbis
Kiesza, Tony Awards 2015
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How did she avoid getting paper cuts? The "Hideaway" singer wore a very busy dress to the 2015 Tony Awards, paying a tribute to white paper everywhere.
Photo: D Dipasupil/FilmMagic/Getty
Heidi Klum, Emmy Awards 2015
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Hey Heidi, did you lose half your dress on the way over? We think this gown could have been stunning without the awkward draping sleeve on her right side. Cover that half of the ensemble with your hand, and she looks AMAZING.
Dencia, Billboard Music Awards 2015
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Woah. Just woah. There aren't even words for this technicolor trip. Dencia looks like she came straight out of a video game, and not in a sexy Tomb Raider type of way.
Amy Poehler, Oscars 2016
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Think of everything you know about Amy Poehler: hilarious, talented, bright, youthful. Now think of the opposite: that's what this dress is. It's the exact opposite of what we'd expect from Amy Poehler, so we can't help but wonder if it's a joke? You got us good, Amy.
Photo: FREDERIC J.BROWN/AFP/Getty Images
Madonna, MET Gala 2016
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Madonna called this outfit a "political statement," posting an Instagram with the caption, "The fact that people actually believe a woman is not allowed to express her sexuality and be adventurous past a certain age is proof that we still live in an age-ist and sexist society." She went on to say that she doesn't care what people think of how she dresses, and she'll keep fighting for women everywhere to have the freedom to portray their bodies however they want. YAS, Madonna! We're all about that life. But, honestly, this dress is ugly regardless of age.
Photo: George Pimentel/WireImage/Getty