The red carpet at the Academy Awards is usually considered hallowed ground. Unlike the Grammys or the MTV Awards, or even the Golden Globes, it is neither the time nor the place for funny business. In fact, it is sometimes, as Sofia Coppola lamented in 2018, too tasteful, too safe, and, sadly, too dull. But, in between the usual fishtail dresses and retro ballgowns, a few fearless women sometimes dare to really wow on the Oscars red carpet. There was Nicole Kidman in 1997, for example—spectacular in chartreuse by John Galliano for Dior. Then there was Marion Cotillard, redefining the meaning of fishtail gowns in Gaultier couture that actually looked like fish scales. Sharon Stone once turned a Gap button down into a power statement (a look that is still inspiring stars almost three decades later), and Lupita Nyong’o gave us princess dressing without being predictable. As for sheer bravado there’s always Cher, perpetually clad in Bob Mackie and eager to flout the conventions of “tasteful dressing,” or Barbra Streisand accepting her first-ever little gold man in a see-through Arnold Scaasi set. Who knows what new, iconic dresses will appear on the upcoming Oscar’s red carpet and join these lists of greats? While we wait to find out, here are the 50 most memorable looks from Academy Awards past.
Rihanna arrived at the 95th Academy Awards on March 12th, 2023 wearing a sheer, latex halter top with an elongated train from Alaïa—but not for long. The star and soon-to-be mother of two changed into a glittering Maison Margiela number to perform her Oscar-nominated song “Lift Me Up” from the film Black Panther: Wakanda Forever.
Nicole Kidman in Armani Privé
Nicole Kidman embodied red carpet chic in this sequined gown from Armani Privé—a look that also featured one of the biggest trends of the night: rosettes.
Cate Blanchett in custom Louis Vuitton
…and a different kind of red carpet chic from Cate Blanchett, who wore custom Louis Vuitton. The asymmetric velvet blouse comes from a never-before-seen archival LV collection; the actress paired it with a jet black skirt made from sustainable silk.
A Sharon Stone reference? We love to see it. At the 2022 Academy Awards, Zendaya wore a satin cropped button-down and a sequined silver column skirt with a bustle train on the back reminiscent of Stone’s famous Oscar ensemble from 1998—comprised of a Gap button down and a purple satin Vera Wang shirt.
Jessica Chastain in Gucci
Jessica Chastain clearly had Tammy Faye, the character she embodied for The Eyes of Tammy Faye (which, incidentally, won her the Best Actress Oscar) in mind when she wore a custom Gucci gown—which channeled Alessandro Michele’s vision for his spring 2022 collection—to the 2022 Oscars.
Billie Eilish in custom Gucci.
Zendaya channeled Cher in this bright yellow Valentino dress at the 2021 Academy Awards.
Not only is Portman’s Dior dress from the 2020 Oscars classic Maria Grazia Chiuri, but the added addition of the embroidered edge of the overcoat, which features the names of snubbed female directors, turned the look into a feminist statement.
Janelle Monae in Ralph Lauren
Monae wore Ralph Lauren to the 2020 Oscars—a hooded gown comprised of 168,000 Swarovski crystals that required 600 hours of hand embroidery to construct.
Chan’s place in the red carpet canon has only gone up since she wore this bubble gum pink Valentino gown to the Academy Awards in 2019.
Lady Gaga in Alexander McQueen
In 2019, Gaga donned custom Alexander McQueen and a 128-carat diamond necklace by Tiffany & Co. that has only been worn by three other people, including Beyoncé and Audrey Hepburn.
Jennifer Lopez in Tom Ford
Lopez managed to stand out while sticking to her usual aesthetic in this disco ball-inspired Tom Ford column dress at the 2019 Academy Awards
Fonda proved herself to be a worthy member of the Balmain Army at the 2018 Academy Awards.
Rita Moreno in Pitoy Moreno
In 2018, Moreno walked the Oscars red carpet in the same black and gold gown she wore to the Oscars in 1962, when she took home the award for Best Supporting Actress.
Cate Blanchett in Armani Privé
Blanchet stunned in this seafoam Armani Privé gown at the 2016 Academy Awards.
The Azzedine Alaïa dress—and gloves—Gaga wore to the 2015 Award ceremony inspired a thousand memes.
Zendaya in Vivienne Westwood
The Euphoria actress fielded unsavory commentary about her choice to wear her hair in locs to the 2015 awards, where she stunned in Vivienne Westwood.
Jennifer Lawrence in Dior
Lawrence’s Dior gown at the 2013 awards will be remembered for many reasons—it’s gorgeous structure, yes, but also the major fall Lawrence took while walking on stage in it to accept her award.
Lupita Nyong’o in Prada
The Us actress looked like Cinderella in Prada at the 86th Annual Academy Awards in 2014.
Streep looked jaw-dropping in this beautifully draped Lanvin dress at the 2012 Oscars.
Gwyneth Paltrow in Tom Ford
At the 84th Annual Academy Awards, Paltrow wowed in a caped Tom Ford column gown.
Angelina Jolie in Atelier Versace
Many have tried to recreate the leg moment this dress allowed from Jolie at the 84th Annual Academy Awards in 2012, but so far, no one has succeeded.
Jennifer Lawrence in Calvin Klein
Lawrence could have gone big for her first Oscars in 2011, but instead she said so much more in this beautifully simple Calvin Klein dress.
Penelope Cruz in Atelier Versace
The actress chose an Atelier Versace gown for the 79th Annual Academy Awards in 2007.
Marion Cotillard in Jean Paul Gaultier Couture
Cotillard stunned at the 80th Annual Academy Awards in 2008 wearing Jean Paul Gaultier couture.
Nicole Kidman in Balenciaga
Kidman’s Balenciaga gown with a bow detail at the back of the neck from the 2007 Oscars proves stars shouldn’t be afraid to wear red on the carpet.
Reese Witherspoon in Vintage Christian Dior
It’s not often stars wear vintage to big events like the Academy Awards, but Witherspoon’s risk paid off when she chose this beautiful embellished gown for the awards in 2006.
Hilary Swank in Guy Laroche
The real magic of this Guy Laroche dress comes from the complete open back, which Swank showed off at the 77th Annual Academy Awards in 2005.
Diane Keaton in Ralph Lauren
No one has personal style quite like Keaton, as she proved in this three-piece menswear-inspired suit with a bowler hat at the 76th Annual Academy Awards.
Jennifer Lopez in Valentino
Lopez wore this one-shoulder mint green dress to the 75th Annual Academy Awards in 2003.
To collect her Best Actress award—as the first Black woman ever to do so—Berry wore a sheer Elie Saab gown at the 74th Annual Academy Awards in 2002.
Julia Roberts in Valentino
We know. We can’t believe it’s taken this long into the gallery to get to Julia Roberts wearing Valentino at the 2001 Oscars, either.
To really drive the point home at the 2001 Oscars, Björk mimicked giving birth to an egg on the red carpet wearing this unforgettable Marjan Pejoski dress.
Cate Blanchett in John Galliano
At the 71st Annual Academy Awards in 1999 Blanchett opted for this intricate John Galliano dress with an open back.
Gwyneth Paltrow in Ralph Lauren
Paltrow was wearing this iconic Ralph Lauren gown to the Oscars in 1999 when she took home the award for Best Actress.
Who could forget the backward Dior tuxedo at the 71st Annual Academy Awards in 1999?
Sharon Stone in Gap and Vera Wang
Ever the envelope-pusher, Stone wore a Gap shirt paired with a Vera Wang skirt to the 70th Annual Academy Awards in 1998.
No one was as cool as Ryder in the ‘90s. Case in point: this black beaded Chanel dress she wore to the Oscars in 1997.
Tiara or no tiara, Hayek still looked like a princess in this Armani column dress in 1997.
Nicole Kidman in Christian Dior by John Galliano
At the 69th Annual Academy Awards in 1997, Kidman would forever change red carpet dressing by sporting this flawless, devastating silk gown in iridescent chartreuse that immediately appalled Joan Rivers and upstaged Tom Cruise.
Uma Thurman in Prada Barbar Tfank
The Pulp Fiction actress was nominated for her role in Quentin Tarantino’s film in 1995—but it was her lilac Prada dress designed by Barbar Tfank that made headlines following that year’s Academy Awards.
Madonna wore Bob Mackie and $20 million worth of Harry Winston diamonds at the 63rd Annual Academy Awards in 1991.
Who could forget Cher’s one-of-a-kind Bob Mackie headpiece from the 1986 Oscars?
The only way Ross could have made this beaded, sheer gown more fabulous was by adding a fur stole, just as she did in 1982.
Farrah Fawcett in Stephen Burrows
The actress, known for her golden blonde locks, chose slinky and metallic for the 1978 Academy Awards.
Hutton’s sherbert-colored Halston gown she wore to the awards in 1975 is the epitome of ‘70s fashion.
Audrey Hepburn in Givenchy
The Roman Holiday star stuck with her go-to designer of the era, Givenchy, in 1975.
Kim Kardashian recreated this look, which Cher wore to the 45th Annual Academy Awards in 1973, for Halloween.
Barbra Streisand in Arnold Scaasi
Streisand shocked some when she accepted her Best Actress Award in sequin see-through bell-bottom pants with a matching top at the 1969 Academy Awards.
Kelly wore mint Givenchy at the 1955 Oscars, where she won Best Actress for her role in the 1954 film The Country Girl.
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