By Cara Sprunk
10:00am PDT, Mar 10, 2024
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In honor of the 96th Academy Awards on March 10, 2024, we're taking a look back at some of the greatest Oscar fashion moments over the years, starting with arguably the all-time most iconic look…
Gwyneth Paltrow won the Oscar for best actress for her work in "Shakespeare in Love" — and topped the best-dressed list — at the 1999 Academy Awards.
Keep reading to see her famous pink gown in all its glory, then read on to see more of the best Oscar fashion moments from over the years…
MORE: Follow Wonderwall on MSN for more fun celebrity & entertainment photo galleries and content
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Remember when Angelina Jolie's leg stole the spotlight on the red carpet at the Academy Awards? How could we forget! The actress famously posed with her leg at an odd angle, popping out from the thigh-hight slit in her glamorous black strapless Atelier Versace gown at the 2012 Oscars. It's a shame her posing distracted from the stunning dress, which truly made a statement on its own.
MORE: Worst Oscar fashion of years past
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Julia Roberts won the Oscar for best actress for her performance in "Erin Brockovich" at the 2001 Academy Awards. She wore a vintage black-and-white Valentino gown for the occasion. All these years later, the actress is still holding on to it. "It's under my bed, in a box," she told People magazine in 2017. "I have this little space in my house that my husband refers to as the heritage collection. Things I go, 'I can't get rid of [this], what about [my daughter] Hazel?'"
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Lily James stunned at the 2022 Oscars in this show-stopping Atelier Versace number: a pale pink floral-embellished confection with a thigh-high slit and a tulle skirt that trailed elegantly behind her.
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Sharon Stone really went outside the box at the 1998 Oscars: She seemingly broke every fashion rule when she walked the red carpet wearing a white Gap button-down shirt — which belonged to then-husband Phil Bronstein — tucked into a lilac Vera Wang skirt.
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Billy Porter made jaws drop — and sparked some amazing conversations — when he arrived on the red carpet at the 2019 Academy Awards in a beautifully tailored tuxedo-inspired gown designed by Christian Siriano. "I know that there is activism inside of fashion," he later told Variety. "I'm an activist. I knew that that tuxedo gown at the Oscars would create a conversation surrounding what gender means, what all these rules we put on everybody in life. We've gotten past a problem with women wearing pants. When women wear pants it's powerful," he explained. "When men wear a dress it's disgusting. We're not doing that anymore. I'm not doing it."
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Michelle Williams looked radiant at the 2006 Oscars in a mustard Vera Wang gown with a ruffled neckline and a draped skirt.
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In 1988, Cher won the Oscar for best actress for her performance in "Moonstruck." She claimed her trophy in an outfit that only Cher could get away with: a sheer sparkly black Bob Mackie number that remains one of the award show's most iconic looks ever.
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Angela Bassett was one of the best dressed stars of the 2021 Academy Awards in this bright red Alberta Ferretti gown featuring dramatic oversized sleeves that formed a bow design in the back.
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Nicole Kidman turned heads at the 2007 Oscars with her red Balenciaga gown, which featured a big bow at the neck. The look remains a classic and has even been imitated, with Emma Stone wearing a very similar dress in 2012. (See that next!)
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Five years after Nicole Kidman impressed fashion critics in a cherry red Balenciaga gown featuring a gigantic bow at the neck, Emma Stone hit the 2012 Academy Awards red carpet in a nearly identical look by Giambattista Valli. Though critics were quick to point out the similarities, there was no denying that the bold look was a striking choice even if it wasn't entirely original.
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Less than a month before Grace Kelly married Prince Rainier of Monaco, she made her final appearance in Hollywood at 1956 Oscars. She couldn't have looked more like a princess than she did in this floral-embellished white gown.
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In 2002 — when Halle Berry became the first Black woman to win the Oscar for best actress — she donned this unforgettable Elie Saab gown with a rich wine-hued skirt and a mostly sheer bodice featuring strategic floral embroidery.
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Kate Winslet celebrated the success of "Titanic" at the 1998 Oscars in a rich green Givenchy gown with gold embroidery created by famed designer Alexander McQueen.
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In 1969, Barbra Streisand accepted the Oscar for best actress for her performance in "Funny Girl" in a fairly risqué sheer black set: bell-bottom pants and a matching long-sleeve blouse with white cuffs and a Peter Pan collar featuring a velvety black ribbon tied at the neck.
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Cate Blanchett — who was nominated for best supporting actress for her work in "Carol" that year — looked breathtaking at the 2016 Oscars in a seafoam green Armani Privé gown with floral embellishments comprised of feathers and Swarovski crystals.
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The Giambattista Valli gown that Kacey Musgraves wore to the 2019 Oscars was practically a work of art. The bubblegum pink confection featured a tulle neckline, a bejeweled bow at the waist and tiers of ruffles down the skirt.
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Jennifer Lawrence famously took a tumble up the stairs while en route to accept the Oscar for best actress for her performance in "Silver Linings Playbook" during the 2013 Academy Awards. She blamed the fall on her stunning blush Christian Dior gown, telling Vogue, "Was that on purpose? Absolutely! … What do you mean, 'What happened?' Look at this dress! I tried to walk up stairs in this dress — that's what happened. I think I just stepped on the fabric and they waxed the stairs or something. What went through my mind? A bad word that I can't say. That starts with an F."
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Lupita Nyong'o — who took home the Oscar for best supporting actress for her breakout performance in "Twelve Years a Slave" that year — dazzled in a baby blue Grecian-inspired Prada gown at the 2014 Academy Awards. "The blue reminded me of Nairobi," she explained on the red carpet.
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Carey Mulligan stunned at the 2021 Academy Awards in this Oscar statue-inspired two-piece Valentino design — a bandeau top and a high-waist full skirt crafted from fabric that looked like liquid gold.
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Audrey Hepburn was a vision in white at the 1954 Oscars — where she won the Academy Award for best actress for her work in "Roman Holiday" — in a sleeveless belted A-line dress featuring an embroidered floral motif.
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Cate Blanchett arrived at the 2000 Oscars looking like a goddess in a black Jean Paul Gaultier gown that was anything but basic. She wisely wore decadent gold accessories that played up the delicate gold chains embellishing the open back.
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When Julianne Moore won the Oscar for best actress for her work in "Still Alice" at the 2015 Academy Awards, she did so in a Karl Lagerfeld-designed Chanel dress that was custom made for her by 27 workers who spent 987 hours crafting the stunning strapless gown.
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In 2010, Sandra Bullock took home the Oscar for best actress for her performance in "The Blind Side." She sparkled on and off the red carpet in this metallic Marchesa gown featuring an intricate lace bodice.
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Amy Adams looked like a princess at the 2013 Oscars in a frothy gray-blue Oscar de la Renta gown. The best supporting actress nominee might not have won for her work in "American Hustle" that year but she topped every best-dressed list.
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Lady Gaga wowed at the 2019 Oscars in a glamorous black Alexander McQueen gown with a dramatic silhouette. She completed her look with black leather opera gloves and a showstopper of a necklace featuring the famed Tiffany Yellow Diamond — the rock previously worn by Audrey Hepburn during her "Breakfast at Tiffany's" press tour. In addition to the stone, which weighs more than 128 carats, the necklace also features another 100 carats of white diamonds.
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Cindy Crawford wore a plunging red Versace gown to the 1991 Oscars — which marked the supermodel's first public appearance with then-boyfriend Richard Gere.
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In 1997, 17-year-old Claire Danes drew raves when she arrived at the Oscars in a youthful, modern ensemble from designer Narciso Rodriguez: a baby blue tee and matching bias-cut satin skirt.
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In 2006, Reese Witherspoon took home the Oscar for best actress for her performance as June Carter Cash in "Walk the Line." She accepted her award in a vintage Christian Dior gown from 1955 that she'd found in Paris.
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Anjelica Huston's iridescent scale-patterned Halston dress fit her like a second skin as she accompanied then-boyfriend Jack Nicholson — who was up for best actor for his work in "Chinatown" that year — to the 1975 Academy Awards. "Even though I worked as a Halston model, I had gotten this dress at Neiman Marcus. The awards were on Friday, and [I bought it] on Wednesday," she told Violet Grey.
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The lilac Givenchy gown that Cate Blanchett wore to the 2011 Academy Awards left fans divided, though fashion critics overwhelmingly praised the Australian star's fashion-forward choice, which featured pale purple and yellow leather pearls and crystals framing the bodice and trailing down the skirt from the waist.
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Amy Adams topped many best-dressed lists at the 2008 Oscars in a strapless fishtail gown by Proenza Schouler. Though the frock was beautifully designed and tailored, its dark green hue is what made it truly magical on the redheaded actress.
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Jennifer Lopez had a major princess moment in a blush pearl-embellished Elie Saab gown at the 2015 Oscars.
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Ruth Negga — who was nominated for her work in "Loving" that year — looked red-hot at the 2017 Oscars in a lacy Valentino gown, which she wore with a bejeweled Irene Neuwirth headband and ruby earrings.
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Talk about a million-dollar look! Hilary Swank won the Oscar for best actress for her work in "Million Dollar Baby" at the 2005 Academy Awards while wearing this memorably elegant navy blue backless dress by Guy Laroche.
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Emma Stone color-coordinated with Oscar when she won big for her work in "La La Land" at the 2017 Academy Awards, rocking a gold Swarovski crystal-embroidered gown designed by Riccardo Tisci for Givenchy Haute Couture.
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Lauren Hutton was the epitome of '70s glamour in a pastel rainbow dress by Halston topped with a fur coat at the 1975 Oscars, which she attended with her then-boyfriend, music and film producer Lou Adler.
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Though Kim Basinger's Escada dress at the 1998 Academy Awards, which she attended with then-husband Alec Baldwin, was perhaps unexpectedly demure (and, unfortunately, easily wrinkled), its unusual pistachio green hue made it hard to forget. It also didn't hurt that she wore it when she won the best supporting actress Oscar for her work in "L.A. Confidential."
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Charlize Theron exuded an understated level of elegance in the burnt orange Vera Wang gown that she wore to the Academy Awards in 2000.
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Natalie Portman took home the Oscar for best actress for her work in "Black Swan" at the 2011 Academy Awards. Earlier in the evening, the then-pregnant star showed off her baby bump in a custom Rodarte dress in a rich purple shade that paired perfectly with her fringe earrings.
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Debbie Reynolds looked angelic at the 1958 Oscars in a ballgown with embroidered floral designs across the bodice and stretching up the skirt.
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Penelope Cruz looked like a million bucks at the 2007 Oscars in a strapless Versace dress with a fitted bodice and a drop-waist that gave way to a voluminous skirt featuring feather-like ruffles.
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Naomi Watts dazzled at the 2016 Oscars in this strapless purple-and-blue sequined Armani Privé gown.
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Talk about statement sleeves! At the 40th Annual Oscars in 1957, Julie Andrews rocked a bold black look with a velvety bodice that she accessorized with a tiny brooch.
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Three-time Oscar nominee Dyan Cannon coordinated with her daughter, Jennifer Grant, in lacy white peasant-style dresses at the 1977 Oscars.
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Lady Gaga put a modern twist on Old Hollywood glam at the 2015 Oscars in a show-stopping sparkling white number by Azzedine Alaïa, which she wore with red leather gloves and a bold red lip. The dress was a real labor of love: 25 people worked on it for two weeks!
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Helen Hunt walked the red carpet at the 70th Annual Academy Awards in an ice blue column dress by Tom Ford for Gucci. Later that night, she took home a best actress Oscar for her work in "As Good As It Gets."
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Raquel Welch was seemingly poured into the curve-hugging liquid blue sequined jumpsuit that she wore to the 1979 Oscars — and she couldn't have been any more stunning in the jaw-dropping look.
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Vivien Leigh wore a timeless floral-print dress when she accepted the Oscar for best actress for her performance in "Gone With the Wind" in 1940.
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Three years before she won an Oscar for her performance in "Cold Mountain," Renee Zellweger won style critics' respect when she arrived at the 2001 Academy Awards wearing a bright yellow vintage Lily et Cie gown.
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Elizabeth Taylor wore a tiara, white gloves and a fur stole with the elegant and simple yet timeless gown she donned at the 1957 Academy Awards, where producer Mike Todd — whom she'd married less than two months earlier — won the Oscar for best picture for producing "Around the World in 80 Days."
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Winona Ryder — a best supporting actress nominee for her performance in "The Age of Innocence" that year — wore a slinky beaded and fringed champagne-colored frock to the 1994 Oscars.
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In 1997, Kristin Scott Thomas walked the red carpet at the Oscars in this dramatic black design. Her dress featured a deep V-neck bodice and mesh panelling that would be cool even today!
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Meryl Streep dressed her baby bump at the 1983 Oscars in a beautiful golden gown that was perfect for a winner (she took home the best actress Oscar for her performance in "Sophie's Choice" that year) but still comfortable enough for a mom-to-be.
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In 2014 — the year she won a best actress Oscar for her work in "Blue Jasmine" — Cate Blanchett wore an embellished dress by Armani Privé. The stunning champagne-hued look was estimated to be worth around $100,000.
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Oprah Winfrey looked pretty in pink at the 2015 Oscars in a blush Vera Wang gown, which she wore with coordinating pink statement earrings.
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It was the ultimate '70s look — and it was worn by the ultimate '70s star: Farrah Fawcett. The actress stunned in a slinky gold chainmail dress by designer Stephen Burrows while presenting with Italian actor Marcello Mastroianni at the 50th Annual Academy Awards in 1978.
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Jennifer Aniston was a classic California beauty at the 2015 Oscars in this champagne-colored one-shoulder beaded gown by Versace.
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In 2004, Angelina Jolie hit the Oscars red carpet looking like a modern-day version of an Old Hollywood screen siren. Her glamorous white satin gown with a plunging neckline was designed by Marc Bouwer.
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Mila Kunis absolutely stunned at the 2011 Academy Awards in this lavender chiffon Elie Saab Haute Couture gown with tiered lace detailing and a ribbon waist.
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Lucy Liu made every best dressed list in this graphic red beaded, one-shoulder Versace gown, which she wore to the Oscars in 2000.
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Sally Field's ensemble at the 1980 Oscars — a sheer floral-print jacket tied over a white cocktail-length dress by Bob Mackie — looks downright casual compared to today's Academy Awards style standards. But it's a look anyone who watched Sally win that night — she took home Oscar gold for her performance in "Norma Rae" — won't forget.
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Marion Cotillard looked beautiful in the white Jean Paul Gaultier mermaid-inspired gown that she wore to the 2008 Oscars, where she won the best actress prize for her work in "La Vie en Rose."
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In 1962, Rita Moreno took home the Oscar for best supporting actress for her performance in "West Side Story" and looked great doing it in a black-and-gold dress with a bold skirt fit for a winner.
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The beautiful Calvin Klein Collection dress that Lupita Nyong'o wore to the 2015 Academy Awards — which was created from 6,000 pearls and worth $150,000 — was stolen from her hotel after the ceremony. The thief, who was never caught, eventually returned it, anonymously claiming to TMZ that the pearls were fake. Real or faux, the gown still made Lupita one of the best dressed stars of the night.
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Sarah Jessica Parker would have made Carrie Bradshaw proud in this gown she wore to the 2009 Oscars — a Dior Haute Couture confection.
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Mary Tyler Moore wore a one-sleeve dress to the 53rd Annual Academy Awards in 1981. With its poofy shoulder, textured silver bodice and big lavender bow, the dress was classic '80s — in the best way possible!
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In 1996 when Kate Winslet nabbed her first Oscar nomination (for "Sense and Sensibility"), she brought some much needed brightness to the red carpet in this bold pink Vivienne Westwood gown, which she wore with a magenta stole.
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In 1995, best supporting actress nominee (for "Pulp Fiction") Uma Thurman turned heads in this lilac Prada dress. The minimalistic look was, at the time, the picture of high fashion — and helped put Prada on the map.
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There's a reason why Cate Blanchett landed on this list multiple times: She just looks that good. She drew raves at the 2005 Academy Awards — where she won her first Oscar (for best supporting actress for her performance in "The Aviator") — when she arrived in a pale yellow silk taffeta Valentino gown featuring an unexpected contrasting maroon belt.
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Helen Hunt sparkled at the 2000 Academy Awards in this backless metallic platinum-hued number featuring chunky jeweled detailing framing the bodice.
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Anne Hathaway stunned in a one-shoulder Marchesa gown at the 2008 Oscars.
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Jennifer Garner dazzled in a silver beaded and fringed Oscar de la Renta gown at the Oscars in 2014. The dress gave off major 1920s vibes when she twirled in it on the red carpet.
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In 2009, Beyonce wore a decadent black-and-gold fishtail gown from House of Dereon — her line with mom Tina Knowles. The dress was dramatic, bold and perfect for an occasion like the Oscars.
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Screen legend Lauren Bacall oozed glamour in a strapless red gown featuring a triangle pattern — which she accessorized with a black cape and dazzling diamonds — when she accompanied husband Humphrey Bogart (then up for best actor for his performance in "The Caine Mutiny") to the 27th Annual Academy Awards in 1955.
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In 2012, Octavia Spencer took home an Oscar for best supporting actress for her performance in "The Help." She looked the part of a winner in this hand-beaded ivory silk tulle Tadashi Shoji gown that took 10 people 1,000 hours to make.
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That necklace! Scarlett Johansson's 2015 Oscars look — a curve-hugging emerald green V-neck gown by Versace — was perfectly accessorized with a matching statement necklace.
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Before Charlize Theron won the best actress Oscar for her transformative performance in "Monster" at the 2004 Academy Awards, she won the red carpet in this beaded champagne gown designed by Tom Ford for Gucci that fit her like a second skin and, believe it or not, was even more stunning from the back.
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At the 1984 Academy Awards, "Dynasty" star Joan Collins made a splash in a gown featuring a sparkling red-and-silver beaded bodice, which she paired with diamond earrings and a bold red lip.
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Keira Knightley dressed her baby bump in an embroidered tulle Valentino dress at the 2015 Academy Awards.
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Adele looked beautiful in a beaded black tulle Jenny Packham gown when she won an Oscar for best original song (for "Skyfall" from the Bond movie of the same name) at the 2013 Academy Awards.
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Rachel Weisz looked gorgeous in a strapless champagne-colored Vera Wang dress with a draped bodice and an embellished train at the 2007 Oscars.
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Kerry Washington looked so good, she nearly created a scandal in a coral Oscar de la Renta gown featuring a bejeweled bodice and a flowing train at the 2013 Academy Awards.
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Goldie Hawn — who was accompanied by longtime partner Kurt Russell — wore a slinky, shimmering sleeveless dress to the 1997 Oscars.
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Gisele Bundchen looked ethereal in a strapless white Dior gown with an empire waist at the 2005 Oscars.
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In 1991, Geena Davis channeled Oscar in this gold lace gown with a cinched waist.
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In 2010, Zoe Saldana wore a bold look — this sparkling ombre purple design from Givenchy Couture. People either loved it or hated it!
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Jessica Alba didn't let pregnancy keep her from looking insanely glam at the 2008 Academy Awards. The actress — who was expecting her first child, daughter Honor Warren, at the time — wore a maroon Marchesa gown with beautiful feathered detailing across the bodice.
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Viola Davis, who won the best supporting actress Oscar for her work in "Fences" at the 2017 Academy Awards, matched the red carpet in this gorgeous curve-hugging Armani gown.
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Diane Kruger walked the Oscars red carpet in 2010 in this unique number from Chanel, which featured exquisite ruffles and detailing.
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In 2004, Sienna Miller walked the red carpet in her then-signature boho-chic style with this Grecian Matthew Williamson gown that she accessorized with on-theme accessories.
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Loretta Young was the picture of elegant '80s decadence at the 1982 Academy Awards, where she posed in this shimmery white dress with mega-statement sleeves.
