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The most daring Oscars red carpet looks from the past 50 years

The most daring Oscars red carpet looks from the past 50 years
Cher.Credit: Bettmann / Getty
  • For the past 50 years, celebrities have been wearing daring looks to the Academy Awards.
  • Sometimes the bold looks are considered the worst in history, like Björk's swan dress in 2001.
  • Other daring looks are considered the best, like Halle Berry's see-through gown.

1971: Petula Clark was hard to miss in this matching beaded beanie and dress.

1971: Petula Clark was hard to miss in this matching beaded beanie and dress.
Petula Clark.      Ron Galella/Ron Galella Collection via Getty Images

Clark's purple bead-heavy ensemble wouldn't be out of place at a Mardi Gras celebration.

1972: Isaac Hayes accepted an Oscar in this baby blue, fur-lined suit with a matching ruffled shirt.

1972: Isaac Hayes accepted an Oscar in this baby blue, fur-lined suit with a matching ruffled shirt.
Isaac Hayes.      Bettman/Getty Images

Hayes took home the award for his song "Theme from 'Shaft'" in this eye-catching suit.

1973: Cher bared her abs in this yellow two-piece.

1973: Cher bared her abs in this yellow two-piece.
Cher.      Michael Ochs Archives/Getty Images

Cher's Oscars looks are legendary, but her first memorable outfit was this bright yellow beaded set designed by her longtime collaborator Bob Mackie.

1974: Edy Williams made her Oscars debut in a luxurious fur coat ... and leopard print bikini.

1974: Edy Williams made her Oscars debut in a luxurious fur coat ... and leopard print bikini.
Edy Williams.      Michael Montfort/Michael Ochs Archives/Getty Images

This is Williams' first entry on this list, but certainly not the last. Rocking a bikini to the Academy Awards cemented her place in red carpet history.

1975: Gena Rowlands wore a glitzy pink dress with a matching Little Red Riding Hood-esque cape to accompany John Cassavetes.

1975: Gena Rowlands wore a glitzy pink dress with a matching Little Red Riding Hood-esque cape to accompany John Cassavetes.
John Cassavetes and Gena Rowlands.      Michael Montfort/Michael Ochs Archives/Getty Images

That year, Rowlands was nominated for her performance in "A Woman Under the Influence," which was written and directed by her husband. Although she didn't win, she made a splash with this sparkly gown.

1976: Diane Keaton matched a bright white suit with a striped shirt, a polka dot tie, and a giant carnation in her lapel.

1976: Diane Keaton matched a bright white suit with a striped shirt, a polka dot tie, and a giant carnation in her lapel.
Diane Keaton.      Frank Edwards/Fotos International/Getty Images

While Keaton is famous for embracing menswear now, back in the '70s, this Richard Tylor design was considered "unexpected."

1977: Edy Williams once again stole the show with this look that defies explanation.

1977: Edy Williams once again stole the show with this look that defies explanation.
Edy Williams.      Fotos International/Archive Photos/Getty Images

This year, Williams opted for an almost entirely sheer gown with a bustier top attached with a jewel. She also wore sparkly underwear and yet another fur coat.

1978: Farrah Fawcett took golden goddess to a whole new level with this dress - but one wrong move would've led to a wardrobe malfunction.

1978: Farrah Fawcett took golden goddess to a whole new level with this dress - but one wrong move would
Farrah Fawcett.      Walt Disney Television/Getty Images Photo Archives

Fawcett was the definition of '70s glam that night in this Stephen Burrows gown, which Paper City Mag called "glitzy" but "not in a crass way."

1979: Raquel Welch wore a skintight, royal blue sequined jumpsuit to walk the carpet.

1979: Raquel Welch wore a skintight, royal blue sequined jumpsuit to walk the carpet.
Raquel Welch.      Ron Galella/Ron Galella Collection via Getty Images

Welch was visible from a mile away thanks to this sequined catsuit and huge gold choker.

1980: Dolly Parton wore a revealing look to the Academy Awards this year.

1980: Dolly Parton wore a revealing look to the Academy Awards this year.
Dolly Parton.      ABC Photo Archives / Getty

Parton's low-cut gown with a bedazzled bow was a daring choice.

1981: Edy Williams also wore a low-cut dress to the Oscars red carpet.

1981: Edy Williams also wore a low-cut dress to the Oscars red carpet.
Edy Williams.      Ron Galella / Getty

The actress chose a halter-top dress with a plunging neckline.

1982: Although Liberace only performed at the Academy Awards, his look certainly was bold.

1982: Although Liberace only performed at the Academy Awards, his look certainly was bold.
Liberace.      Michael Ochs Archives / Getty

Liberace's outfit was colorful and covered in beads. The more you looked at it, the more intricate it became.

1983: Genie Francis stood out on the red carpet in this ruffled look.

1983: Genie Francis stood out on the red carpet in this ruffled look.
Genie Francis.      Michael Ochs Archives / Getty

The multi-layered, pink gown certainly was the most daring look of the year.

1984: Joanna Pacula turned heads with a daring yellow bomber jacket.

1984: Joanna Pacula turned heads with a daring yellow bomber jacket.
Joanna Pacula.      Ron Galella / Getty

The actress and model paired the bold jacket with a striped gown.

1985: Prince wore a hooded, bedazzled cape this year.

1985: Prince wore a hooded, bedazzled cape this year.
Prince.      Time & Life Pictures / Getty

Prince accepted an Oscar for "Purple Rain" this year.

1986: Cher stopped the show with her large headdress and matching black ensemble.

1986: Cher stopped the show with her large headdress and matching black ensemble.
Cher.      Credit: Bettmann / Getty

"Remember when actor Don Ameche won an Oscar for Best Supporting Actor in Cocoon?'" CNN wrote in 2020. "Of course not; we were too enchanted by the woman presenting him with a statuette: Cher, in a bat-crazy mash-up of witchy showgirl and Halloween Big Bird."

1987: Helena Bonham Carter turned the iconic Oscars black gown on its head.

1987: Helena Bonham Carter turned the iconic Oscars black gown on its head.
Helena Bonham Carter.      Ron Galella, Ltd. / Getty

"This fluffy black dress isn't that bad ... if you're an overemotional 15-year-old girl who listens to the Cure," Claire Suddath wrote for Time in 2011.

1988: Cher had another memorable look when she took home the Academy Award for best actress.

1988: Cher had another memorable look when she took home the Academy Award for best actress.
Cher.      Ron Galella / Getty

She accepted the Oscar in another Bob Mackie gown, which Harper's Bazaar calls "yet another iconic red carpet look."

1989: Angie Dickinson made a daring choice with this all-white feathered ensemble.

1989: Angie Dickinson made a daring choice with this all-white feathered ensemble.
Angie Dickinson.      Ron Galella, Ltd. / Getty

The Old Hollywood actress' completely feathered skirt was paired with white gloves.

1990: Kim Basinger mixed menswear and red carpet glam in this ... interesting gown.

1990: Kim Basinger mixed menswear and red carpet glam in this ... interesting gown.
Kim Basinger.      Ron Galella/Ron Galella Collection via Getty Images

Basinger actually designed this gown herself, with one half resembling a white suit jacket with an embroidered golden sleeve and the other half a strapless gown with an almost shoulder-length white glove, all tied together with a full ball gown-level skirt.

Time called it "nothing short of a white hot mess."

1991: Debbie Allen wore an iridescent rainbow skirt with a fully beaded top featuring multiple suns.

1991: Debbie Allen wore an iridescent rainbow skirt with a fully beaded top featuring multiple suns.
Jasmine Guy and Debbie Allen.      Ron Galella/Ron Galella Collection via Getty Images

Allen was glowing, just like her dress.

1992: Geena Davis' poofy white high-low dress resembles a wedding dress, but the black straps, tights, and ribbons give it an edge.

1992: Geena Davis
Geena Davis.      Ron Galella/Ron Galella Collection via Getty Images

As It's Rosy wrote, her "Oscar dress felt borderline theatrical," which makes sense, as it was designed by costume designers Ruth Meyers and Bill Hargateat.

1993: Whoopi Goldberg's lime green and purple look was impossible to miss at that year's ceremony.

1993: Whoopi Goldberg
Whoopi Goldberg.      Kevin Mazur/WireImage/Getty Images

At first glance, Goldberg appeared to be wearing a deep eggplant skirt with a green and purple paisley top and a purple jacket — but in reality, her skirt was fully open and lined with lime green, and the shirt was actually a jumpsuit. She also wore matching heels and earrings.

According to The Guardian, the look was inspired by Disney.

1994: Prince accessorized a sheer white jumpsuit with a lollipop and a thick gold chain.

1994: Prince accessorized a sheer white jumpsuit with a lollipop and a thick gold chain.
Prince.      Ron Galella, Ltd./Ron Galella Collection via Getty Images

He also added a cane in typical flamboyant Prince fashion.

1995: Lizzy Gardiner wore a dress entirely made of American Express gold cards.

1995: Lizzy Gardiner wore a dress entirely made of American Express gold cards.
Lizzy Gardiner.      KMazur/WireImage/Getty Images

Gardiner, a costume designer, designed the dress for the movie "Priscilla, Queen of the Desert," but it didn't make the cut. Instead, she wore the dress for Hollywood's biggest night and ended up taking home the Oscar for costume design.

"They all had my name on them, and I joined all the cards together with wire. Full length, and [it] was split almost to the waist because there was no other way of doing it. I had gold underwear on, and off I went," she told ABC News in 2017.

1996: Susan Sarandon's bronze gown made her look like one of the Oscars.

1996: Susan Sarandon
Susan Sarandon.      Kevin Mazur/WireImage/Getty Images

We really haven't seen a color like this on the red carpet, before or since.

1997: Juliette Binoche channeled a vampire with this dramatic collar.

1997: Juliette Binoche channeled a vampire with this dramatic collar.
Juliette Binoche.      Frank Trapper/Corbis via Getty Images

The Chicago Tribune, on the other hand, called it her "coppery 'Snow White' gown." It was designed by Sophie Sitbon.

1998: Cher opted for a completely see-through dress dripping in crystals with a matching crystal hat and choker.

1998: Cher opted for a completely see-through dress dripping in crystals with a matching crystal hat and choker.
Cher.      Ron Galella/Ron Galella Collection via Getty Images

As Harper's Bazaar wrote, she completely "shut down" that year's ceremony in this revealing outfit.

1999: Celine Dion wore a backwards white satin tuxedo with no shirt and a giant white hat.

1999: Celine Dion wore a backwards white satin tuxedo with no shirt and a giant white hat.
Celine Dion.      Kevin Mazur/WireImage/Getty Images

Of Dion's John Galliano for Christian Dior tuxedo, Vogue wrote, "It was so bizarre, it was beautiful. It remains on every iteration of Oscars worst dressed lists, but almost two decades later, nobody has forgotten this act of fashion resistance. There should be one like it every year."

2000: Cate Blanchett wore a backless gown to her second-ever Oscars red carpet.

2000: Cate Blanchett wore a backless gown to her second-ever Oscars red carpet.
Blanchett in 2000.      KMazur/WireImage/Getty Images

She accessorized the back-baring, floor-length Jean Paul Gaultier gown with gold jewelry.

2001: Björk made headlines when she showed up on the red carpet with a swan around her neck.

2001: Björk made headlines when she showed up on the red carpet with a swan around her neck.
Björk.      Steve Granitz / Getty

"It is precisely this outlandishness that made the look so iconic," Marianna Cerini at CNN wrote in 2019. "The dress not only secured Björk's place as one of the entertainment business' most memorable personalities, it proved that even terrible dresses can make fashion history."

2002: When accepting her Academy Award, Halle Berry showed off one of the most iconic and most daring Oscars dresses in history.

2002: When accepting her Academy Award, Halle Berry showed off one of the most iconic and most daring Oscars dresses in history.
Halle Berry.      Steve Granitz / Getty

"Aside from her historical win, her Oscar-winning dress instantly became iconic and it arguably put designer Elie Saab, on the map," E! News wrote in 2020.

2003: Hilary Swank went with a lopsided, pink ombre gown for this red carpet.

2003: Hilary Swank went with a lopsided, pink ombre gown for this red carpet.
Hilary Swank.      Kevin Winter / Getty

"It looks like Hilary thought her pale pink mini dress wasn't up to the occasion, so she looked around until — aha! — she found a piece of hot pink gauze to wrap around herself," Victoria Lowe at Cosmopolitan wrote in 2011.

2004: Uma Thurman made the daring decision to be the worst dressed on the Oscars red carpet this year.

2004: Uma Thurman made the daring decision to be the worst dressed on the Oscars red carpet this year.
Uma Thurman.      L. Cohen / Getty

"Everyone looked the same. Everyone had it down to such a perfect T…You get bored. That's when you have to say, 'I will be worst-dressed,'" the actress said, according to Time magazine.

2005: Melanie Griffith showed off her broken foot and a cane on the Oscars red carpet.

2005: Melanie Griffith showed off her broken foot and a cane on the Oscars red carpet.
Melanie Griffith.      Dan MacMedan / Getty

The actress didn't let her broken foot stop her from showing off this Versace dress.

2006: Charlize Theron's emerald gown was boldly accentuated with a large bow on her shoulder.

2006: Charlize Theron
Charlize Theron.      Jeff Kravitz / Getty

The criss-cross stitching and confusing bottom made for a truly daring look.

2007: Kelly Preston opted for head-to-toe cheetah print.

2007: Kelly Preston opted for head-to-toe cheetah print.
Kelly Preston.      Jeff Kravitz / Getty

The dress was made by Dolce and Gabbana.

2008: Marion Cotillard accepted her Academy Award in a memorable white gown.

2008: Marion Cotillard accepted her Academy Award in a memorable white gown.
Marion Cotillard.      Jeff Kravitz / Getty

"Marion Cotillard took home the award for best actress at the 80th Annual Academy Awards dressed like a modern day mermaid in this intricately detailed, ivory-colored custom Jean Paul Gaultier gown," Chrystin Bunion at W wrote in 2017.

2009: Instead of going with the traditional Oscars gown, Tilda Swinton chose a daring top and bottom ensemble.

2009: Instead of going with the traditional Oscars gown, Tilda Swinton chose a daring top and bottom ensemble.
Tilda Swinton.      Kevin Mazur / Getty

The look was designed by Lanvin.

2010: Zoe Saldana's Givenchy feathered gown clashed with the jeweled top ... but in the best way.

2010: Zoe Saldana
Zoe Saldana.      Kevin Mazur/WireImage/Getty Images

"The voluminous gown has it all: Sparkle, ombré, countless floating layers of tulle, and pops of saturated color. Amongst the sea of black and metallic, this show-stopper topped my best-dressed list," wrote Violet Moon Gaynor of Elle.

2011: Madonna chose a black bodysuit with a sheer lace overlay and a fur stole for the red carpet.

2011: Madonna chose a black bodysuit with a sheer lace overlay and a fur stole for the red carpet.
Madonna.      Christopher Polk/VF11/Getty Images for Vanity Fair

Madonna was 52 years old when she rocked this bodysuit that left her "butt cheeks exposed," as The Hollywood Reporter wrote — and she looks great doing it.

2012: Sacha Baron Cohen rolled up to the red carpet dressed as his character from "The Dictator," complete with the "ashes" of Kim Jong-il.

2012: Sacha Baron Cohen rolled up to the red carpet dressed as his character from "The Dictator," complete with the "ashes" of Kim Jong-il.
Sacha Baron Cohen.      Michael Buckner/Getty Images

2013: Nicole Kidman's gold and black sequined gown looked like it was made of liquid - until you see the bottom's golden swirls.

2013: Nicole Kidman
Nicole Kidman.      Jason Merritt/Getty Images

PopSugar called the dress, designed by L'Wren Scott, an "exquisite creation."

2014: Lupita Nyong'o made her Oscars debut with a robin's egg blue gown that became a statement for her red carpet style in the years to come.

2014: Lupita Nyong
Lupita Nyong'o.      Axelle/Bauer-Griffin/FilmMagic/Getty Images

Although we've seen many bold looks in this list, there's something to be said for a simple color choice like this one — Nyong'o continues to be a breath of fresh air on the red carpet seven years after she made her Oscars debut in this plunging Prada gown.

2015: Irina Shayk's slinky black dress was actually a mesh jumpsuit with a one-sided skirt.

2015: Irina Shayk
Irina Shayk.      Alberto E. Rodriguez/WireImage/Getty Images

Shayk's look was designed by Atelier Versace.

2016: Kate Winslet quite literally shimmered on the red carpet with this silk lamé look.

2016: Kate Winslet quite literally shimmered on the red carpet with this silk lamé look.
Kate Winslet.      Gregg DeGuire / Getty

The strapless gown was custom-made by Ralph Lauren.

2017: Janelle Monáe made her Oscars red carpet debut in a show-stopping number.

2017: Janelle Monáe made her Oscars red carpet debut in a show-stopping number.
Janelle Monáe.      Steve Granitz / Getty

"For Janelle Monáe's first trip to the Academy Awards, she didn't hold back," Janelle Okwodu at Vogue wrote in 2017. "Arriving in an ornate Elie Saab Haute Couture fairy-tale gown and layers of diamonds, Monáe provided the evening with its most dramatic red-carpet moment."

2018: Actress Haley Bennett chose a gown that prominently featured a large patch of grass.

2018: Actress Haley Bennett chose a gown that prominently featured a large patch of grass.
Haley Bennett.      Frazer Harrison / Getty

Christian Dior crafted this avant-garde dress.

2019: Billy Porter broke boundaries when he wore a tuxedo top and a large velvet skirt.

2019: Billy Porter broke boundaries when he wore a tuxedo top and a large velvet skirt.
Billy Porter.      Dan MacMedan / Getty

At the time, Christian Allaire at Vogue wrote that the Christian Siriano gown was "a play on masculinity and femininity, the look challenged the rigid Hollywood dress code and was boundary-pushing in all the right ways."

2020: Janelle Monáe returned to the Oscars wearing a stunning bedazzled, hooded look that turned heads on the red carpet.

2020: Janelle Monáe returned to the Oscars wearing a stunning bedazzled, hooded look that turned heads on the red carpet.
Janelle Monáe.      Steve Granitz / Getty

The Ralph Lauren gown was covered in 168,000 Swarovski crystals.

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