25 Most Revealing Oscar-Night Looks

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Cher

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Consider Cher the ultimate rule breaker, with one exception — when it comes to Oscar outfits, less is decidedly more. As in less fabric, more skin. And without a doubt, many of Cher’s looks are now utterly iconic, ranging from a gold, genie-inspired outfit with midriff-baring top and embellished skirt (1973) and a flower power two-piece ensemble (1974). In 1986, Cher upped the ante with that infamous feathered Mohawk and S&M black sequined bra and in ’88 opted for Cleopatra glam in a sheer, black Bob Mackie creation that left little to the imagination. —Nina Terrero

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Gwyneth Paltrow

Sebastian Artz/Getty Images

Paltrow may be Hollywood royalty but at the 2002 Academy Awards, the actress went for a goth look by Alexander McQueen that failed to reign on the red carpet thanks to its unflattering, see-through bodice. —Nina Terrero

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Pamela Anderson and Elizabeth Hurley

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Repeat offender Hurley (keep clicking for more examples) looks practically chaste next to to the former Baywatch babe. Let’s just say paparazzi bulbs weren’t doing all the flashing at Vanity Fair‘s 2001 after-party. —Lanford Beard

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Halle Berry

S Granitz/WireImage

Berry embraced her sexpot status at the 2002 Oscars in an Elie Saab dress with a transparent top that might have been a recipe for disaster — if it hadn’t been for some strategically placed embroidery. —Nina Terrero

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Barbra Streisand

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Streisand took home an Oscar in 1969 for her performance in Funny Girl but her sequined black Scaasi jumpsuit — complete with a white Peter Pan collar and cuffs — was seriously cutting-edge, including a peek-a-boo glimpse of Streisand’s black hot pants and bra. —Nina Terrero

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Selma Blair

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The designer who readied Blair’s frock for Vanity Fair‘s 2002 party clearly had Cruel Intentions toward fabric. —Lanford Beard

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Charlize Theron

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Theron made jaws drop when she walked onto the red carpet at the 2000 Oscars in a V-neck orange Versace gown that showed off some seriously sexy décolletage. But her plunging neckline was nothing compared to the deeply cut, ruched detailing of the dress’s back, which showed off Theron’s best, ahem, assets. —Nina Terrero

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Farrah Fawcett

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In 1978, Fawcett brought Studio 54 glam to the Oscars, dressed to boogie in a slinky, oh-so-glam gold open-back Stephen Burrows gown. Aspiring actresses take note: While Fawcett definitely skipped the bra (was it cold that night?), she did so with nary a nip slip. —Nina Terrero

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Madonna

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We saw London, we saw France, we saw Her Madgesty’s underpants…at Vanity Fair‘s 2011 fête. —Lanford Beard

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Cindy Crawford

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Crawford looked every inch the supermodel when she showed up at the 1991 Oscars in a red plunging, halter-necked Versace gown. And while she may have been accompanied with one of the hottest on-screen stars of the ’90s, Richard Gere, in that now-infamous dress Crawford ensured that all eyes were on her — or on her cleavage, anyway. —Nina Terrero

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Angelina Jolie

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It was the sexy leg pose ogled ’round the world — or at least the World Wide Web. Donning a slinky Atelier Versace dress, Jolie upped the va-va-voom factor in 2012 with her provocative posing. —Erin Strecker

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Elizabeth Hurley and Elle Macpherson

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Two different approaches, two times the skin! The model-turned-actresses’ flesh-baring philosophies were the yin to each other’s yang at Vanity Fair‘s 2000 bash. —Lanford Beard

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Taraji P. Henson

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It must have been pretty hard for Henson to Hustle and Flow at the 2005 Oscar after-parties in that dress. —Erin Strecker

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Brandi Glanville

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Donning her own design in 2013, Real Housewives of Beverly Hills‘ Glanville made sure the camera couldn’t look away when she made her Oscar debut. —Erin Strecker

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Liberty Ross

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Based on this slinky number from the 2013 Vanity Fair shindig, it would appear the model-turned-scorned-woman has an undergarment policy as free as her name. —Lanford Beard

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Demi Moore

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Consider Moore’s 1989 Oscars look — comprised of a black spandex bike shorts, bustier top and brocade evening gown combo — early fodder for Joan Rivers’ now-infamous red-carpet commentary. But it was the late ’80s and, to her credit, Moore learned from her fashion don’t and has steered clear from wearing gym gear on the red carpet again. —Nina Terrero

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Jada Pinkett-Smith

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When it came to the crop top trend of the late ’90s, few rocked the look as well as Pinkett-Smith, who wore a belly-baring metallic green top and skirt combo to the 1997 Academy Awards. Pinkett-Smith accessorized with simple stud earrings, a few silver bracelets and husband Will — who was dressed in perfect prom style in a matching green dress shirt. —Nina Terrero

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Irina Shayk

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When choosing gowns for her appearances at the 2012 and 2013 Vanity Fair after-parties, Shayk clearly embraced the ”If you’ve got it flaunt it” philosophy she honed while appearing in the 2007-13 Sports Illustrated Swimsuit issues. —Lanford Beard

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Geena Davis

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In 1992, Davis was nominated for Thelma & Louise and celebrated by donning a ’90s twist on French can-can girl style. Her ruffled party dress proved without a doubt that so-called ”sexy” period costume should be reserved for film — not the red carpet. —Nina Terrero

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Ashley Judd

ABC

Judd went for classic Hollywood glam in her white Richard Tyler gown, complete with a sky-high slit. But it was the slit itself that helped cement this look as one of the most revealing in Oscars history, as the actress gave the audience a glimpse of her lady bits when she strolled on stage to present an award. —Nina Terrero

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Jena Malone

Gregg DeGuire/WireImage

Before booking Catching Fire, Malone sent out sparks with this hot little number at Vanity Fair’s big event in 2011. —Lanford Beard

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Jennifer Hudson

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Four years after her Best Supporting Actress win for Dreamgirls, a Versace-clad Hudson might as well have told reporters that she is not going anywhere without a body-hugging gown that debuted her new figure in 2011. —Erin Strecker

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Heather Mills

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At least we can consider the former Mrs. Paul McCartney a trendsetter in one respect — she made underboob a thing way before Rihanna ever did with a two-piece, midriff-baring lace dress that left little to the imagination. —Nina Terrero

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Heidi Klum

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The gown Klum donned for Elton John’s viewing party in 2013 probably would’ve been better at the Golden Globes, don’t you think? —Lanford Beard

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Björk

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Björk cemented her place in ”Worst Dressed” history with the frothy swan frock she wore to the 2001 Oscars, proving that even a hint of sex appeal — those peekaboo cuts at the chest and tummy! —? couldn?t rescue the freakish concept of an animal worn as a dress.—Nina Terrero

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25 Most Revealing Oscar-Night Looks

1 of 26

Cher

2 of 26

Gwyneth Paltrow

3 of 26

Pamela Anderson and Elizabeth Hurley

4 of 26

Halle Berry

5 of 26

Barbra Streisand

6 of 26

Selma Blair

7 of 26

Charlize Theron

8 of 26

Farrah Fawcett

9 of 26

Madonna

10 of 26

Cindy Crawford

11 of 26

Angelina Jolie

12 of 26

Elizabeth Hurley and Elle Macpherson

13 of 26

Taraji P. Henson

14 of 26

Brandi Glanville

15 of 26

Liberty Ross

16 of 26

Demi Moore

17 of 26

Jada Pinkett-Smith

18 of 26

Irina Shayk

19 of 26

Geena Davis

20 of 26

Ashley Judd

21 of 26

Jena Malone

22 of 26

Jennifer Hudson

23 of 26

Heather Mills

24 of 26

Heidi Klum

25 of 26

Björk

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