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Faith Hill
REX/Shutterstock Faith Hill really missed the mark in this multicolor gown from the 2002 Oscars. (REX/Shutterstock)
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Vera Farmiga
REX/Shutterstock Vera Farmiga had us puzzled with this strapless, majorly ruffled gown in 2010.(REX/Shutterstock)
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Zoe Saldana
REX/Shutterstock The top of Zoe Saldana’s, 2010 Oscars dress was gorgeous, but once it turned to the purle hue and ruffled out, we were let confused. (REX/Shutterstock)
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Sandy Powell
REX/Shutterstock Sandy Powell wore a metallic pantsuit to the 2016 Oscars, and it’s just not really doing it for us. (REX/Shutterstock)
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Heidi Klum
REX/Shutterstock Heidi Klum usually stuns on the red carpet, but this purple gown did nothing flattering for her. (REX/Shutterstock)
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Janelle Monae
REX/Shutterstock At the 2017 Oscars, Janelle Monae’s dress was ALL over the place. (REX/Shutterstock)
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Lady Gaga
REX/Shutterstock Lady Gaga wore red gloves to the 2015 Oscars, and they totally took away from her look. (REX/Shutterstock)
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Cher
REX/Shutterstock That headpiece! That crop top! Everything about tihs outfit Cher wore in 1986! (REX/Shutterstock)
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Blanca Blanco
REX/Shutterstock Blanca Blanco oozed sex appeal in this look, but the color, pattern and sleeves really just ruined the look. (REX/Shutterstock)
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Cher
REX/Shutterstock Cher loves to take red carpet risks, but at the Oscars, it doesn’t always translate. This sheer look from 1988 is a bit TOO out there. (REX/Shutterstock)
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Bjork
REX/Shutterstock Bjork’s swan dress from 2001 is talked about to this day. (REX/Shutterstock)
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Uma Thurman
REX/Shutterstock Uma Thurman’s 2001 Oscars look was just all over the place. (REX/Shutterstock)
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Tyra Banks
REX/Shutterstock Tyra Banks’s metallic, purple ballgown was a bit too out-there for the Oscars. (REX/Shutterstock)
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Selma Blair
REX/Shutterstock While the Oscars are meant for glamorous ballgowns, Selma Blair went a different route in this red ensemble. (REX/Shutterstock)
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Sarah Jessica Parker
REX/Shutterstock Carrie Bradshaw would not approve of this look Sarah Jessica Parker wore to the Oscars.(REX/Shutterstock)
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Melissa McCarthy
REX/Shutterstock Melissa McCarthy didn’t quite nail this red carpet look. (REX/Shutterstock)
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Kate Hudson
REX/Shutterstock Kate Hudson’s teal blue dress didn’t quite fit in at the Oscars. (REX/Shutterstock)
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Kate Winslet
REX/Shutterstock Kate Winslet hadn’t quite nailed her red carpet style when she wore this look to the Oscars.(REX/Shutterstock)
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Jennifer Hudson
REX/Shutterstock Jennifer Hudson’s style has definitely evolved since this bizarre Oscars look. (REX/Shutterstock)
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Jennifer Lopez
REX/Shutterstock Jennifer Lopez always looks like a queen, but this certainly wasn’t her best. (REX/Shutterstock)
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Hilary Swank
REX/Shutterstock Hilary Swank had us all confused with this mini dress covered in sheer pink tulle at the Oscars. (REX/Shutterstock)
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Charlize Theron
REX/Shutterstock Charlize Theron did nothing to flatter her fabulous figure in this purple Oscars outfit. (REX/Shutterstock)
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Cameron Diaz
REX/Shutterstock Oh, Cameron Diaz, what were you thinking? (REX/Shutterstock)
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Madonna
REX/Shutterstock Madonna was a bit too eclectic for the Oscars in this ensemble (REX/Shutterstock)
