By Cara Sprunk
8:00pm PST, Mar 11, 2023
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In honor of the 95th Annual Academy Awards on March 12, 2023, we’re revisiting the best looks to ever to grace the Oscars red carpet…
Angelina Jolie let her right leg do the talking through the high slit in the black Atelier Versace gown that she wore to the 2012 Oscars. The bold pose was so popular that a Twitter account and countless memes were even created in honor of it!
MORE: Worst Oscar fashion of years past
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Julia Roberts won a best actress Oscar for her performance in “Erin Brockovich” wearing a black-and-white vintage Valentino gown that remains one of the most memorable of all time. 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?'”
MORE: Most iconic dresses in movie history
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Lily James stunned in this show-stopping Atelier Versace number — a pale pink floral-embellished confection with a thigh-high slit and a glamorous tulle skirt that trailed behind her — at the 2022 Oscars.
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In 1998, Sharon Stone broke all of the Oscars’ sartorial rules — and impressed fashion critics — when she arrived at the Academy Awards wearing then-husband Phil Bronstein’s white button-down shirt from the Gap 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 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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In 2006, Michelle Williams walked the red carpet in one of the most iconic Oscar dresses of all time. Accompanied by then-love Heath Ledger, the new mom was radiant in this canary yellow Vera Wang gown.
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In 1988, Cher won the best actress Academy Award for her performance in “Moonstruck” in an outfit that only Cher could get away with — a sheer, sparkly black number designed by Bob Mackie — that remains one of the most iconic Oscar looks ever.
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Angela Bassett was one of the best dressed stars of the night at 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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In 2007, Nicole Kidman turned heads with the large bow on her red Balenciaga gown. The look remains a classic and has even been imitated, with Emma Stone wearing a very similar dress in 2012.
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Five years after Nicole Kidman impressed style critics in a cherry red Balenciaga gown featuring a gigantic bow, 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 last appearance in Hollywood at the 28th Annual Academy Awards in 1956. She couldn’t have looked more like a princess than she did in this floral-embellished white gown.
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The white Tom Ford gown with a floor-length cape that Gwyneth Paltrow wore to the 2012 Academy Awards wasn’t just one of the most talked-about looks at the Oscars that year — it was also one of a handful of Oscar dresses that proved to be ahead of its time.
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In 2002, Halle Berry became the first African American woman to win a best actress Oscar and she did it in this iconic wine-hued Elie Saab dress that featured a sheer floral-embroidered bodice.
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Kate Winslet celebrated the success of “Titanic” at the 70th Annual Academy Awards in 1998 in a rich green Givenchy gown with gold embroidery created by famed designer Alexander McQueen.
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Barbra Streisand accepted her best actress Oscar for her performance in “Funny Girl” in 1969 in a fairly risqué sheer black pantsuit with a memorable and prim white Peter Pan collar and cuffs.
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Nominated for best supporting actress for her work in “Carol” at the 88th Annual Academy Awards in 2016, Cate Blanchett looked breathtaking in a seafoam green-blue floral feathered gown by Armani Privé with clusters of Swarovski crystals sewn into it.
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The Giambattista Valli gown that Kacey Musgraves wore to the 2019 Oscars was an actual work of art. The bubblegum pink confection started with a unique tulle turtleneck feature before giving way to ruffled tulle bordering the sleeves. From there, a fitted bodice featured a bedazzled bow at the waist before it all fanned out into a fluffy tiered tulle skirt.
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At the 2013 ceremony, Jennifer Lawrence won the best actress Oscar for her performance in “Silver Linings Playbook.” While her blush-hued Christian Dior Couture dress made a splash on the red carpet, its real notoriety came when she fell on her way to the stage to accept her award. “Was that on purpose? Absolutely,” she joked to Vogue after the fall. “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 an Oscar for best supporting actress for her breakout performance in “Twelve Years a Slave” at the 2014 ceremony, dazzled in this sky blue Grecian-inspired gown from Prada. “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 high-waisted full skirt crafted from fabric that draped like it was liquid gold.
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Audrey Hepburn was the picture of glamour and innocence when she won the best actress Oscar for her work in “Roman Holiday” in 1954. Her pale floral-patterned dress was cinched at the waist in classic Hepburn style.
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Gwyneth Paltrow has worn many beautiful gowns on the Oscars red carpet (plus a few unfortunate frocks), but in 1999, she donned her most radiant look ever. The best actress winner (for “Shakespeare in Love”) channeled Grace Kelly in this pink Ralph Lauren ball gown, which was credited with helping to bring pink back into fashion.
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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. Cate was smartly styled in decadent gold accessories that played up the delicate gold chains the designer used to embellish the gown’s stunning open back.
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When Julianne Moore won a best actress Oscar 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 gown.
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In 2010, Sandra Bullock took home a best actress Oscar 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 when she wore 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 channeled Old Hollywood in a glamorous black look by Alexander McQueen at the 2019 Oscars. Despite opting for a classic color, the superstar’s gown was anything but boring thanks to its dramatic silhouette. She also upped the glam factor when it came to accessories, adding leather opera-length gloves and a showstopper of a necklace featuring the famed Tiffany Yellow Diamond, the rock previously worn by one of the most famous ladies in film history, Audrey Hepburn, when she promoted “Breakfast at Tiffany’s.” The main stone weighs more than 128 carats plus the necklace features another 100 carats of white diamonds.
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Cindy Crawford wore a plunging red Versace gown to the Oscars in 1991. It was 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 on the Oscars red carpet 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 an 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 a best actor Oscar for his work in “Chinatown,” to the 1975 Academy Awards ceremony. “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 couture lilac Givenchy gown that Cate Blanchett wore to the 2011 Academy Awards left fans divided — but fashion critics overwhelmingly praised the Australian star’s fashion-forward choice, which featured pale purple and yellow leather pearls and crystals on its back and bodice.
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In 2008, Amy Adams made all the Oscar best dressed lists 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 looked like a fairy tale princess at the 2015 Oscars in an ethereal yet sexy pearl-embellished blush ball gown by Elie Saab Haute Couture.
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At the 89th Annual Academy Awards in 2017, Ruth Negga — who was nominated for her work in “Loving” — had an exquisite look from head to toe. She paired her custom red lace-embellished Valentino dress with a jeweled Irene Neuwirth headband and ruby earrings and, like many others, added an ACLU blue ribbon as the finishing touch.
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Talk about a million-dollar look! Hilary Swank won the best actress Oscar 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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When Emma Stone won for her work in “La La Land” at the 2017 Academy Awards, her outfit was perfectly coordinated with her Oscar. The best actress winner stunned in 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 ceremony, 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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At the 2011 Academy Awards, Natalie Portman took home a best actress statue for her performance in “Black Swan.” The 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 in a grand ball gown with beautiful detailing on the skirt when she performed at the Oscars in 1958.
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At the 2007 Academy Awards, Penelope Cruz looked like a million bucks in a feathered blush-hued dress by Versace.
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At the 2016 Oscars, Naomi Watts dazzled in this strapless purple-and-blue sequined Armani Privé strapless gown. Naomi and her stylist narrowed down their options and let her then-partner, Liev Schreiber, make the final choice. Clearly he has good taste!
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Talk about statement sleeves! At the 40th Annual Oscars in 1957, Julie Andrews wore this chic, bold black look that she accessorized with a tiny brooch.
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Three-time Oscar nominee Dyan Cannon brought daughter Jennifer Grant to the 1977 Oscars ceremony. The two matched in white but Dyan undeniably stole the show in her sheer white off-the-shoulder dress.
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At the 2015 Oscars, Lady Gaga channeled Old Hollywood (minus those red leather gloves) in a show-stopping sparkling white number by Azzedine Alaïa. The dress was a real labor of love: 25 people worked on it for two weeks!
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At the 70th Annual Academy Awards, Helen Hunt walked the red carpet 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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The night Vivien Leigh accepted a best actress Oscar for her performance in “Gone With the Wind” in 1940, she wore a timeless floral-patterned dress.
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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 for the 1957 Oscars where producer Mike Todd — whom she’d married less than two months earlier — won the best picture Academy Award 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,” wore a slinky beaded and fringed champagne-colored frock to the 66th Annual Academy Awards in 1994.
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In 1997, Kristin Scott Thomas walked down 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 55th Annual Academy Awards in 1983 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’s greatest Oscars dress came in 2015 — a blush-colored Vera Wang stunner. The “Selma” producer, whose movie was nominated for best picture, added some serious bling to the look to amplify it.
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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 dress with tiered lace detailing and a ribbon waist by Elie Saab Haute Couture.
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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 fakes. 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-sleeved 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, but was a gem nonetheless.
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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 corset gown.
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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 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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At the 2000 Academy Awards, Helen Hunt sparkled in this backless metallic platinum-hued number featuring chunky jeweled detailing framing the bodice.
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Anne Hathaway wore a favorite Oscars color — red — in 2008, when she stunned in a one-shoulder Marchesa gown.
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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. 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, gloves 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 — an 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 gown by Jenny Packham when she won an Oscar for best original song (for her “Skyfall” Bond theme) at the 2013 Academy Awards.
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Rachel Weisz looked gorgeous in a strapless champagne-colored Vera Wang dress with detailing on the bust 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 jeweled bodice and flowing train at the 2013 Academy Awards.
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Goldie Hawn, accompanied by longtime partner Kurt Russell, wore a slinky, shimmering halter dress to the 1997 Oscars.
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Gisele Bundchen walked the Oscars red carpet with then-boyfriend Leonardo DiCaprio in 2005. While her gold-embroidered white Dior gown tended to billow, nothing could look truly unflattering on the supermodel, especially a dress like this.
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In 1991, Geena Davis wore this cinched lace gown with gold foiling to the Oscars. The flattering dress was perfect for an event celebrating a gold statuette.
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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 expecting her first child, Honor Warren, wore a maroon Marchesa gown with beautiful feathered detailing across the chest.
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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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Talk about boho chic! In 2004, Sienna Miller walked the red carpet in her signature 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.
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