Published February 29, 2012 by wieneragnes
Photo: Getty

Uma Thurman in Christian Lacroix, 2004   Aye, aye, Uma! No, this isn’t a runaway extra from the latest Pirates of the Caribbeaninstallment. While Ms. Thurman usually makes the most of her lean, statuesque frame, in 2004 she chose to walk the fashion plank in this risky, swashbuckling milkmaid number that had most fashion critics jumping ship.     Photo: Inspirations and Elations Sharon Stone in Vera Wang and Gap, 1998   In what’s become known as the epitome of a risky fashion ‘do,’ Sharon Stone showed the world that mixing high fashion with high street can make a maximum impact. Stone’s casualGap button-down (paired with a lilac Vera Wang skirt) came right out of her then-husband’s closet– thus also inspiring many walk-of-shame ensembles for years to follow.

Photo: Moviefone

Barbra Streisand in Arnold Scaasi, 1969   Babs generally plays it safe nowadays, but back in the ’60s, she collected her Best Actress Oscar (for Funny Girl) clad in glittery, flare-legged, see-through pajamas. Though she later claimed that she hadn’t realized the unusual ensemble was so sheer, we don’t really believe her. You’re still a risk-taker in our eyes, Barbra.

Photo: Disboards.com

Kim Basinger in her own design, 1990   Kimmy B. looked like a Disney princess on crack in this new wave, asymmetrical ball gown, which she designed for herself to wear to the Academy Awards in 1990. Designing your own Oscar gown is a risk in itself. Designing it after you’ve been on a week-long bender of The Little Mermaid viewings and wine cooler consumption is an even greater risk. Though we can’t really agree it’s one worth taking.     Photos: Getty Hilary Swank in Guy Laroche, 2005   Hilary went an unconventional route with her 2005 Guy Laroche gown, proving a toned back can be just as sexy (and probably more so) as Hollywood’s old standby, over-exposed breast implants. In fact, it was Hil’s othercleavage that nearly made a showing. If you know what I’m saying…


Photo: Ew.com

Jada Pinkett Smith in Versace, 1997

First of all, IT WAS THE ’90s. So let’s try to focus on the positives here. Not everyone can pull-off a matching 2-piece mermaid club-kid ensemble – let alone to the biggest night in Hollywood. And she accessorized with a belly chain. You go, Jada.

Photo: Cherrific.com

Cher in Bob Mackie, 1986

Cher and Bob Mackie go together like a feather headdress and exposed hip bones at the Oscars. We’re not even sure if this little number is considered “risky” by Cher standards, but in our world, it’s up there.

Photo: Telegraph.co.uk

Cher in Bob Mackie, 1988

This was actually pretty conservative Cher-fare back in the day, but we couldn’t notinclude it. We wish we could turn back tiioooome and have more crazy outfits like this at today’s Oscars.

Photo: Getty

Charlize Theron in Dior, 2011

We always look forward to seeing what fashion risk-taker Charlize is wearing come Oscar night. She must’ve known she’d be sending mixed fashion messages with her rosey-bossomed Dior gown in 2011, but she had the guts to rock it anyway. When the fit of a gown (and of course, the wearer) is this flawless, you can get away with some unconventional details.

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