VivaVibe

Cher

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

Gwyneth Paltrow

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

Pamela Anderson and Elizabeth Hurley

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

Halle Berry

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

Barbra Streisand

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

Selma Blair

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

Charlize Theron

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

Farrah Fawcett

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

Madonna

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

Cindy Crawford

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

Angelina Jolie

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

Elizabeth Hurley and Elle Macpherson

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

Taraji P. Henson

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

Brandi Glanville

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

Liberty Ross

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

Demi Moore

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

Jada Pinkett-Smith

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

Irina Shayk

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

Geena Davis

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

Ashley Judd

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

Jena Malone

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

Jennifer Hudson

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

Heather Mills

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

Heidi Klum

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

Björk

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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