The 15 Riskiest Oscar Red Carpet Looks of All Time

It's hard to believe, but the granddaddy of all red carpet events - THE ACADEMY AWARDS! - is only two days away. Can you tell we're excited? Really, we are. Obviously, our favorite part of the entire evening is the arrivals: Who's there, and more importantly, who they're wearing. Above all, we want to see who's bold enough to take the fashion risks - because those are the dresses we'll be talking about the next morning. And those who really make a mark could end up on a list like this one in twenty years time! Behold, our choices for the fifteen riskiest red carpet Oscar looks of all time. Some are great, some... not so much. But the best ones are an amazing combination of both. Read on as we take a look back at some of the most fashionably daring dames on Hollywood's biggest night.
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It's hard to believe, but the granddaddy of all red carpet events - THE ACADEMY AWARDS! - is only two days away. Can you tell we're excited? Really, we are. Obviously, our favorite part of the entire evening is the arrivals: Who's there, and more importantly, who they're wearing. Above all, we want to see who's bold enough to take the fashion risks - because those are the dresses we'll be talking about the next morning. And those who really make a mark could end up on a list like this one in twenty years time! Behold, our choices for the fifteen riskiest red carpet Oscar looks of all time. Some are great, some... not so much. But the best ones are an amazing combination of both. Read on as we take a look back at some of the most fashionably daring dames on Hollywood's biggest night.
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It's hard to believe, but the granddaddy of all red carpet events - THE ACADEMY AWARDS! - is only two days away. Can you tell we're excited? Really, we are. Obviously, our favorite part of the entire evening is the arrivals: Who's there, and more importantly, who they're wearing. Above all, we want to see who's bold enough to take the fashion risks - because those are the dresses we'll be talking about the next morning. And those who really make a mark could end up on a list like this one in twenty years time!

Behold, our choices for the fifteen riskiest red carpet Oscar looks of all time. Some are great, some... not so much. But the best ones are an amazing combination of both. Read on as we take a look back at some of the most fashionably daring dames on Hollywood's biggest night.

Photo: Getty

Photo: Getty

Uma Thurman in Christian Lacroix, 2004

Aye, aye, Uma! No, this isn't a runaway extra from the latest Pirates of the Caribbean installment. 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

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 casual Gap 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

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

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

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 other cleavage that nearly made a showing. If you know what I'm saying...

Photo: Getty

Photo: Getty

Gwyneth Paltrow in Alexander McQueen, 2002

Gwynnie was widely criticized for her straight-from-the-runway, exceptionally bra-free McQueen look, but we applaud her for trying something different. After all, this is the same girl who several years earlier donned that bubblegum Ralph Lauren prom dress to the Oscars. But that posture, G... please.

Photo: Ew.com

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

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

Photo: Telegraph.co.uk

Cher in Bob Mackie, 1988 This was actually pretty conservative Cher-fare back in the day, but we couldn't not include it. We wish we could turn back tiioooome and have more crazy outfits like this at today's Oscars.

Photo: Getty

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.

Photo: Getty

Photo: Getty

Celine Dion in John Galliano, 1999

It's still unclear whether Canadian queen Celine actually wore her Galliano suit backwards or if that was just the design of it -- either way, this cris-crossed look is a fashion risk that has stood the test of time. And that hat is pretty badass. Unrelated: How much does she look like Jennifer Aniston here?

Photo: Getty

Photo: Getty

Cate Blanchett in Givenchy Couture, 2011

Cate's 2011 Oscar dress managed to be extremely subdued and risque at the same time, with many fashion critics split down the middle in a heated debate. Though there definitely was some sort of an egg-framing boob element happening (we're not sure what that means either) in this out-of-the-ordinary, high fashion look, it perfectly showcased her amazingly toned arms and the light lilac really complimented her skin tone. We hope risk-taker Cate gave herself a flab-free pat on the back for this one.

Photo: Strawberryicecream.com

Photo: Strawberryicecream.com

Bjork in Marjan Pejoski, 2001

The Oscar risk to end all others: Whether she wants to or not, whimsical Icelandic singer Bjork will never be able to live down (like, say, a down comforter) what has probably become the most parodied dress in history. She even carried a little egg-shaped purse. We think this risk is absolutely presh, and we're very grateful she wore a bra.

Photo: Getty

Photo: Getty

Halle Berry in Elie Saab, 2002

In 2002, Halle Berry was the first black woman ever to win the Best Actress award - and she did so wearing this Adam and Eve-esque Elie Saab gown that just barely covered the essentials. Even though this dress might seem more memorable now than risky, its overall sheerness is still pretty R-rated for the generally conservative Academy Awards crowd.

Photo: Getty

Photo: Getty

Angelina Jolie in Versace, 2000

Before Angelina stole away Brad and saved all the world's dying children (by adopting them, der), she was just another goth girl who kept her husband's blood in a vile and made out with her brother. Wearing your Morticia Addams Halloween costume to the Academy Awards-- even if it's by Versace-- is a pretty huge risk in itself. But we're happy Angie was willing to take it.