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The 39 Most Talked About Oscars Dresses of All Time

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The 92nd Academy Awards will recognize the best of the best on Sunday, February 9, 2020. While we can’t wait to see which actors head to the stage to accept a coveted golden statuette this year, we’ll also be looking forward to seeing all of Hollywood’s biggest stars walk the red carpet before heading into the Dolby Theatre.

With nearly a century’s worth of Oscars history to look back on, we’re taking this opportunity to reminisce on the most memorable outfits through the years — especially the ones that have inspired extreme reactions, both good and bad. From Cher’s signature sequins to Anne Hathaway’s distractingly-darted dress, the Academy Awards have seen no shortage of controversial red carpet fashion choices.

Scandalous Oscars Dresses - Bette Davis

Bette Davis, 1936

The Dangerous star was so convinced she wouldn’t win Best Actress, she wore an old costume to the ceremony — a plain navy dress. After her surprise victory, rival Joan Crawford reportedly sniped, “Dear Bette! What a lovely frock.”

Scandalous Oscars Dresses - Barbra Streisand

Barbra Streisand, 1969

Barbra made history tying with Katharine Hepburn for Best Actress, but that wasn’t the only memorable moment of the night. The Funny Girl star apparently didn’t realize the bright lights would turn her sequined pant suit transparent.

Scandalous Oscars Dresses - Cher

Cher, 1974

Cher wore a midriff-baring ensemble the year before, but this flowery bandeau top exposed a lot more than just her abs.

Scandalous Oscars Dresses - Edy Williams

Edy Williams, 1974

So many questions: Is that a leopard-print bikini? What’s with the fur coat? And can someone please explain the dog?

Scandalous Oscars Dresses - Farrah Fawcett

Farrah Fawcett, 1978

The ’70s style icon wowed in a slinky gown by Stephen Burrows.

Scandalous Oscars Dresses - Cher

Cher, 1986

Designer Bob Mackie didn’t hold back making this legendary sequined ensemble complete with a sky-high feathered headdress.

Scandalous Oscars Dresses - Edy Williams

Edy Williams, 1986

More than a decade after gracing the red carpet in a bikini, Edy decided to take an even more daring approach. Carefully arranged strands of pearls leave very little to the imagination in this outfit.

Scandalous Oscars Dresses - Cher

Cher, 1988

None of the Kardashians can pull off a naked dress quite like this. The Goddess of Pop won her first Oscar for Moonstruck that year, wearing another Bob Mackie creation.

Scandalous Oscars Dresses - Demi Moore

Demi Moore, 1989

It was the ’80s, but Demi really should have steered clear of bicycle shorts while designing this ensemble herself.

Scandalous Oscars Dresses - Kim Basinger

Kim Basinger, 1990

The Batman actress also tried her hand at fashion that year, dreaming up this, ahem, interesting suit-ballgown hybrid.

Scandalous Oscars Dresses - Cindy Crawford

Cindy Crawford, 1991

The supermodel attended the 63rd Academy Awards with new boyfriend Richard Gere in tow. The plunging sheath by Versace still tops best-dressed lists more than two decades later.

Scandalous Oscars Dresses - Geena Davis

Geena Davis, 1992

She may have won acclaim for Thelma and Louise, but Geena didn’t hear much praise for this bustier top-and-ruffled skirt combo.

Scandalous Oscars Dresses - Whoopi Goldberg

Whoopi Goldberg, 1993

Underneath the comedian’s purple satin skirt was a pair of paisley pants and a blindingly-green lining.

Scandalous Oscars Dresses - Lizzy Gardiner

Lizzy Gardiner, 1995

American Express didn’t want the costume designer using their brand in The Adventures of Priscilla, Queen of the Desert, but they had no problem providing 254 expired cards for a one-of-a-kind Oscars dress. The real question is, how did she sit down?

Scandalous Oscars Dresses - Susan Sarandon

Susan Sarandon, 1996

Something about the ’90s inspired celebs to wear sunglasses both indoors and at night, but Susan’s shades were the least of her problems in this shiny (and brown!) halter top.

Scandalous Oscars Dresses - Ashley Judd

Ashley Judd, 1998

Years before Janet Jackson’s infamous wardrobe malfunction, Ashley made headlines after an up-to-there slit revealed a little too much for primetime television.

Scandalous Oscar Dresses

Cher, 1998

At this point, it would be more scandalous if Cher didn’t wear something revealing to the Oscars. This shimmery number maintained the trend, from outlandish headdress to beaded hem.

Scandalous Oscars Dresses - Charlize Theron

Charlize Theron, 2000

Charlize wowed in a tangerine gown by Vera Wang, but the actress later claimed the bombshell moment had an unintended effect. “I can’t tell you how many times I’ve auditioned for a role, only to have my agent come back and say, ‘Listen, Charlize, they saw you in the orange dress and they don’t think you can do it,'” she explained.

Scandalous Oscars Dresses - Edy Williams

Edy Williams, 2000

The consistently-daring actress was back at it again in what can only be described as a figure skater’s ensemble gone wrong.

Scandalous Oscars Dresses - Matt Stone and Trey Parker

Matt Stone & Trey Parker, 2000

The creators spoofed Jennifer Lopez’s infamous Grammys moment and Gwyneth Paltrow’s princess gown in an extremely memorable Oscars debut.

Scandalous Oscars Dresses - Björk

Björk, 2001

No Academy Awards article would be complete without Bjork’s iconic swan dress. Ellen DeGeneres spoofed it. Kevin James wore one. Valentino even riffed the theme in its 2014 spring collection. But no one can ever top the musician “laying an egg” on the red carpet. Ever.

Scandalous Oscars Dresses - Kate Hudson

Kate Hudson, 2001

The press skewered Kate Hudson’s Oscars debut, hating on everything from the Stella McCartney cape to the extremely-curly hair. But the young actress didn’t pay any mind to the criticism. “I felt so beautiful, and I have it in my closet still to the day,” she said at a 2012 Vogue event.

Scandalous Oscars Dresses - Gwyneth Paltrow

Gwyneth Paltrow, 2002

Although she later regretted not wearing a bra, Gwyneth still likes her “goth” look by Alexander McQueen. Unfortunately, few critics could get over the sheer top and heavy eyeliner.

Scandalous Oscars Dresses - Halle Berry

Halle Berry, 2002

The Monster’s Ball star also opted for a transparent bodice, but her Elie Saab dress (with strategic embroidery) received glowing praise. It’s now routinely cited as one of the best Oscars dresses of all time.

Scandalous Oscars Dresses - Hilary Swank

Hilary Swank, 2005

Thanks to a daring backless gown, the Best Actress nominee drew the inevitable comparison of looking like a million bucks.

Scandalous Oscars Dresses - Sally Kirkland

Sally Kirkland, 2007

Former Best Actress nominee Sally Kirkland is always an Oscars personality, but a circus tent on top of some precarious pasties is a real head-scratcher.

Scandalous Oscars Dresses - Tilda Swinton

Tilda Swinton, 2008

Cosmo later wrote, “Please save Tilda from the black velvet garbage bags holding her body hostage.” It’s safe to say she did not make the best dressed list.

Scandalous Oscars Dresses - Charlize Theron

Charlize Theron, 2010

Charlize usually nails the red carpet, but bloggers hated the conspicuously-placed rosettes on her Dior gown.

Scandalous Oscars Dresses - Madonna

Madonna, 2011

Fans wanted to know where Madge put her pants, but a black leotard under a see-through skirt seems quite tame by today’s standards.

Scandalous Oscars Dresses - Jennifer Lawrence

Jennifer Lawrence, 2011

Jennifer would go on to cement herself in Oscars history (), but this Calvin Klein number attracted plenty of attention — and comparisons to Jessica Rabbit.

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