The Oscars' Most Unforgettable Looks

By Instyle
Updated Jun 21, 2011 @ 12:57 pm
Kevin Mazur/Jason Nevader/WireImage

The Oscars' Most Unforgettable Looks

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Zoe Saldana, 2010

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Zoe Saldana

chose an otherworldly Givenchy couture gown that combined a sparkling bodice with clouds of sculpted tulle.

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Halle Berry, 2002

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Halle Berry

knows how to do classy and sexy. The night she won an Oscar for Monster's Ball, the actress highlighted her amazing figure with a peek-a-boo embroidered gown from Elie Saab.

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Bjork, 2001

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Oscar dress as performance art? The boundary-pushing Bjork channeled a swan in a Marjan Pejoski ensemble, even going so far as to drop golden eggs along the red carpet.

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Diane Keaton, 2004

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Diane Keaton

took her signature boy-meets-girl Annie Hall aesthetic a step further with a Chaplin-esque suit and bowler from Ralph Lauren. Points for consistency!

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Demi Moore, 1989

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Back in the late eighties, Demi Moore took a chance on an unknown stylist-herself. Rumor has it the actress had a hand in designing her tapestry-lined gown and lace-edged biker shorts.

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Gwyneth Paltrow, 2002

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In contrast to the pretty pink ballgown in which she won her 1999 Academy Award, Gwyneth Paltrow chose an edgy black Alexander McQueen top and gathered taffeta skirt.

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Cher, 1986

Photo by Eugene Adebari / Rex USA

The multi-talented Cher doesn't mess around when it comes to making red-carpet statements. Her long-time collaborator (since the days of Sonny and Cher!) Bob Mackie designed a showgirl-worthy beaded black two-piece with a towering 2-foot headpiece made of rooster feathers.

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Uma Thurman, 2004

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Uma Thurman

wore a couture Christian Lacroix ensemble-and got called Swiss Miss. "It was a beautiful dress," Thurman told InStyle. "Turns out I wore it wrong."

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Geena Davis, 1992

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Nominated for Thelma and Louise, Geena Davis embodied frothy early-'90s style in a gams-baring ruffled minidress courtesy of costume designers Ruth Meyers and Bill Hargate.

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Kim Basinger, 1990

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Presenter Kim Basinger got creative and designed her own white satin ensemble. The full-skirted gown was topped with a half-jacket that featured cryptic lettering down its single sleeve. Perhaps a tribute to her symbol-loving then-beau Prince?

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Barbra Streisand, 1969

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Hello gorgeous! Barbra Streisand revealed more than she bargained for in sequined Scaasi evening pajamas. "I didn't realize the outfit was so see-through," she told InStyle. "You couldn't tell that in the dressing room, only under the bright lights." Luckily, she had an attention-grabbing accessory-a Best Actress Oscar for her role in Funny Girl.

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Whoopi Goldberg, 1993

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This funny lady stole the spotlight when she presented at the 65th Annual Academy Awards. Bought at a Beverly Hills boutique, Whoopi Goldberg's purple satin frock coat opened to reveal a green lining and slim brocade trousers.

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Jada Pinkett Smith, 1997

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With abs like that, it's no wonder Jada Pinkett Smith wanted to show them off. Her mesh metal Versace two-piece revealed the actress's flawless shape-and fashion daring.

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Faith Hill, 2002

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When you're going to sing "Somewhere Over the Rainbow" at the Oscars, who can blame you for choosing a sorbet-hued gown? Singer Faith Hill took on the legendary Wizard of Oz tune in a pastel Versace design.

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Angelina Jolie, 2000

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A winner for Girl, Interrupted, Angelina Jolie got gothic in a long-sleeved Versace gown and pitch-black hair extensions.

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Celine Dion, 1999

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Singer Celine Dion tried out a twist on menswear-a 180-degree twist, that is. She showed her major flair for the dramatic in a backwards tuxedo from Christian Dior.

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Hilary Swank, 2003

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Taking a break from bold statement gowns, Hilary Swank chose a ballerina-inspired tulle Christian Dior gown and had her custom shoes dyed to match.

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Sharon Stone, 1998

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This one's all about the mix- Sharon Stone paired a lilac Vera Wang evening skirt with a button-down Gap shirt right out of her then-husband's closet.

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