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Demi Moore – 1989
Biker shorts were one of the most popular lower body coverings of the ‘80s, but it takes a truly bold woman to bring these Tour de France fashions to the biggest black tie affair of the season.
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Barbra Streisand – 1969
Every celeb who now regularly wears a naked dress on the red carpet should bow down to this icon, who was sporting fully sheer fashions decades before most of them were even born.
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Whoopi Goldberg – 1993
Whoopi’s Oscars dress is the equivalent of a couture mullet—business purple ball gown on top, party paisley pants on the bottom.
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Jada Pinkett Smith – 1997
While we could easily see this look being worn today by Rihanna or any number of next generation supermodels, at the time Jada Pinkett-Smith’s green, liquid metal Versace crop top and maxi skirt (complete with belly chain and coordinated hubby) were nothing short of scandalous.
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Celine Dion – 1999
While Celine Dion is currently experiencing a bit of a sartorial renaissance, the backwards white tuxedo she wore in 1999 proves she’s never not been a red carpet queen.
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Björk - 2001
For better or worse, Björk's swan dress is undeniably one of the most memorable and maligned Oscars dresses of all time.
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Gwyneth Paltrow – 2002
While this dress isn’t all that unusual (especially in comparison to some of the other looks in this gallery), for Gwyneth this goth McQueen gown was far more Wednesday Addams than her usual glamorous Grace Kelly vibes. For the record, she still regrets not wearing a bra that night.
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Faith Hill – 2002
Surely, there is no dress more appropriate to perform “Somewhere Over the Rainbow” in than this technicolor ombré column.
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Uma Thurman – 2004
The Oscars were alive with the Sound of Music when Uma Thurman attended in this dirndl-inspired gown.
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Lady Gaga – 2015
While opera gloves were once black tie de rigeur, Gaga’s very specific red ones had everyone rushing to make comparisons, ranging from a Palmolive commercial to Cruella de Vil.
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Lizzy Gardiner – 1995
The Oscar-winning costume designer’s dress cut right to the chase: it costs a lot of money to look this good. Well, unless your dress is made entirely out of gold American Express cards, that is … in which case it probably still requires a pretty high spending limit.
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Isaac Hayes – 1971
Men’s suiting doesn’t involve nearly enough fun fur accents, as Isaac Hayes proved in this suit with ruffled cuffs, fluffy baby blue lapels and a matching fur bow tie.
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Trey Parker and Matt Stone – 2000
When attending your first Oscars, it’s best to take a style cue from the red carpet pros, like these two South Park creators did, recreating Jennifer Lopez and Gwyneth Paltrow’s iconic ensembles.
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Dennis Rodman – 1997
The basketball player has never met a flourish he didn’t like, accessorizing his brocade blue tux with a crushed velvet top hat, ruffled sleeves, pocket watch, and a swipe of matching blue eyeshadow just for good measure.
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Juliette Lewis – 1992
While the actress’s ensemble was pure "classic debutante" thanks to the sheath dress and long single-strand pearls, her beauty look was pure ‘90s hip hop with a head full of unexpected cornrows.
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Cher -1973 and 1974
For Cher, the Oscars have always been all about the abs, from her first time attending in a yellow bejeweled bandeau and the tropical bikini top and sarong she wore the very next year…
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Cher - 1986, 1988 and 1998
To the showgirl phase of her career during which she wore two of her most memorable looks of all time, a black bedazzled bra and skirt complete with feathered headpiece and a similar belly dancer-esque sheer, spangled dress. Almost a decade later, she returned to the ceremony in yet another futuristic chapeau and semi-sheer gown.