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
Image Credit: Evan Agostini/Getty Image
Taylor Swift
Miley Cyrus
Rihanna
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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 BeardImage Credit: Stefanie Keenan/Getty Images
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
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- 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
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Before booking Catching Fire, Malone sent out sparks with this hot little number at Vanity Fair’s big event in 2011. —Lanford Beard
Image Credit: Gregg DeGuire/WireImage
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- 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 TerreroImage Credit: Ron Galella/WireImage
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
Image Credit: Jim Smeal/WireImage
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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
Image Credit: Jim Smeal/WireImage
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
Image Credit: Jordan Strauss/Invision/AP
Lady Gaga
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- 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 StreckerImage Credit: Steve Granitz/WireImage
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 BeardImage Credit: J. Vespa/WireImage
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 StreckerImage Credit: Gregg DeGuire/FilmMagic
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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 TerreroImage Credit: Ron Galella/WireImage
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We saw London, we saw France, we saw Her Madgesty’s underpants…at Vanity Fair‘s 2011 fête. —Lanford Beard
Image Credit: Jon Kopaloff/FilmMagic
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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 TerreroImage Credit: Sebastian Artz/Getty Images (2)
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 TerreroImage Credit: S Granitz/WireImage
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 TerreroImage Credit: Sebastian Artz/Getty Images
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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
Image Credit: (L-R) Getty Images; WireImage; Getty Images; AP
Cher’s infamous sartorial risks, Ashley Judd’s wardrobe malfunction, Pam Anderson’s ultra-casual ”Vanity Fair” ensemble, more daring duds from Hollywood’s biggest night
Melissa Rivers
Meghan Trainor
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
Image Credit: Gregg DeGuire/WireImage
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
Paris Hilton
