The Most Outrageous Oscars Gowns of All Time

When we say that stars take Oscars night as an opportunity to make a statement on the red carpet, some really make a statement. We're not talking about Old Hollywood glamour, either. We've highlighted the the more out-there, liberal numbers that have gone down in history as the most unforgettable.
  1. 1.
    BARBRA STREISAND, 1969
    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." Luckily, she had an attention-grabbing accessory-a Best Actress Oscar for her role in Funny Girl.
  2. 2.
    DIANA ROSS, 1973
    Ross chose a custom satin Bob Mackie and Ray Aghayan design for her Lady Sings the Blues nod. "Diana had a little boy's body," Mackie told the Los Angeles Times of their choice to go menswear. "She was bone thin and looked wonderful in pants."
  3. 3.
    CHER, 1986
    Cher's long-time collaborator Bob Mackie designed a showgirl-worthy beaded black outfit with a cashmere cape, sparkling loincloth and a towering 2-foot headpiece made of over 800 rooster feathers. Making her dazzling appearance onstage, she cracked: "As you can see, I did receive my Academy booklet on how to dress like a serious actress."
  4. 4.
    DEMI MOORE, 1989
    Back in the late '80s, Demi Moore took a chance on an unknown stylist - herself. The actress had a hand in designing her tapestry-lined gown and lace-edged biker shorts.
  5. 5.
    KIM BASINGER, 1990
    Presenter Basinger 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?
  6. 6.
    GEENA DAVIS, 1992
    Nominated for Thelma and Louise, Davis embodied frothy early-'90s style in a gams-baring ruffled minidress courtesy of costume designers Ruth Meyers and Bill Hargate.
  7. 7.
    WHOOPI GOLDBERG, 1993
    Bought at a Beverly Hills boutique, Goldberg's purple satin frock coat opened to reveal a green lining and slim brocade trousers.
  8. 8.
    JADA PINKETT SMITH, 1997
    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.
  9. 9.
    CELINE DION, 1999
    Dion showed her major flair for the dramatic in a backwards tuxedo from John Galliano for Christian Dior, accented with a Dior by Stephen Jones topper and Ray-Bans studded with diamonds by Martin Katz. "Ray-Ban said if I wore these they would give $50,000 to my cystic fibrosis charity, so you better believe I wore them," said the singer.
  10. 10.
    ANGELINA JOLIE, 2000
    A winner for Girl, Interrupted, Angelina Jolie got gothic in a long-sleeved Versace gown and pitch-black hair extensions. "It's silky and very me," she said of the dress, adding, "I wouldn't have the patience for real hair this long."
  11. 11.
    BJORK, 2001
    The boundary-pushing Bjork channeled a swan in a Marjan Pejoski ensemble, even going so far as to drop golden eggs (designed by artist boyfriend Matthew Barney) along the red carpet.
  12. 12.
    GWYNETH PALTROW, 2002
    In contrast to the pretty pink ballgown in which she won her 1999 Academy Award, Gwyneth Paltrow chose an sheer black Alexander McQueen top, gathered taffeta skirt and stiletto boots. Although she received lots of criticism for the style switch-up, the designer was pleased with the effect. "She looked incredible," he said of the look, which was altered from a long-sleeved fall 2002 runway design.
  13. 13.
    HALLE BERRY, 2002
    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 up-and-coming designer Elie Saab.
  14. 14.
    DIANE KEATON, 2004
    Keaton took her signature boy-meets-girl Annie Hall aesthetic a step further with a Chaplin-esque suit and bowler from Ralph Lauren.
  15. 15.
    HILARY SWANK, 2003
    Taking a break from bold statement gowns, Hilary Swank chose a ballerina-inspired tulle Christian Dior dress. John Galliano was responsible for the custom design and Tod’s dyed an evening bag to match.
  16. 16.
    UMA THURMAN, 2004
    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."
  17. 17.
    FAITH HILL, 2002
    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 gave a nod to the legendary Wizard of Oz tune with her pastel Versace design. "Since she was wearing black onstage, we wanted to do something colorful for the carpet," her stylist Garth Condit told People.
  18. 18.
    DIABLO CODY, 2008
    The screenwriter stayed true to her personal style and rocked a wild Christian Dior gown on the red carpet. Later that night, Cody won her first Oscar: Best Original Screenplay for Juno.
  19. 19.
    ZOE SALDANA, 2010
    Zoe Saldana chose an otherworldly Givenchy couture gown that combined a sparkling bodice with clouds of sculpted tulle. "It just embodied everything I've been through in this Avatar dream," she told reporters.
  20. 20.
    CHARLIZE THERON, 2010
    The actress arrived in a lilac-hued Dior gown and fashion critics were immediately divided. Some applauded the risky draping on the couture dress, while others panned the design.
  21. 21.
    HELENA BONHAM CARTER, 2011
    Best Supporting Actress nominee Helena Bonham Carter collaborated with her Alice in Wonderland costume designer Colleen Atwood on this 1880s-inspired black velvet gown that she paired with Solange Azagury-Partridge earrings and a Lulu Guinness fan-shaped clutch.
  22. 22.
    HELEN HUNT, 2013
    Why is this simple navy dress outrageous? Because it's from HampM! The always glamorous actress shocked red carpet critics by opting out of couture and into affordable fashion.
  23. 23.
    LADY GAGA, 2015
    Lady Gaga made a daring choice when she selected a glittering Alaïa dress with daring red gloves.