What 66 Celebrities Wore When They Won Their First Oscar
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The Academy Awards are coming up, and honestly all we can hope and pray for is that the presenters get everyone's names actually right this year. While there's no telling what awkwardness, red carpet fails, and live TV flubs we might be in store for—especially if John Travolta shows up, bless—one thing is certain: the fashion will be lit. Or totally atrocious. Honestly, every year is an unpredictable and exciting adventure!
Picking out the dress to wear while potentially/hopefully/please-fingers-crossed taking home a freaking gold Oscar statue is obviously a huge deal, so let's take a look back at 50 actresses who nailed their winning look—or at the very least, wore something memorable, even if it looked vaguely 👀.
Vivien Leigh
The year: 1940
The Win: Best Actress, Gone with the Wind
The Look: Vivien wore a stunning evening gown by Irene Gibbons, a famous costume designer who was a fave of Marlene Dietrich and Greta Garbo. She accessorized the look with a Van Cleef & Arpels necklace—a very chic gift from her then-fiancé Laurence Olivier.
Ingrid Bergman
The Year: 1945
The Win: Best Actress, Gaslight
The Look: Damn, what a departure from the norm! Instead of an over-the-top gown, Ingrid wore a simple skirt and top with sandals. And fun fact: this movie is credited for coining the term "gaslighting" (it's about a woman whose husband convinces her she's going crazy when he's, in fact, manipulating her).
Audrey Hepburn
The Year: 1954
The Win: Best Actress, Roman Holiday
The Look: Audrey's delicate dress from her favorite designer Givenchy is one of the most famous Oscar gowns of all time. The cinched waist? The boat neck? The belt?! Your faves simply shouldn't even bother.
Grace Kelly
The Year: 1955
The Win: Best Actress, The Country Girl
The Look: Vertigo costume designer Edith Head is responsible for this stunning gown, and it was said to be the most expensive Oscars dress ever at the time—it cost $4,000.
Elizabeth Taylor
The Year: 1961
The Win: Best Actress, Butterfield 8
The Look: Christian Dior, of course. Apparently Elizabeth's fourth husband Eddie Fisher bought this dress for her, along with “almost the entire collection.”
Julie Andrews
The Year: 1965
The Win: Best Actress, Mary Poppins
The Look: Julie collected her first Oscar in a pale yellow dress by an unknown designer, and I think we can all agree she looked like a knockout. Maria Von Trapp could never!
Goldie Hawn
The Year: 1970
The Win: Best Supporting Actress, Cactus Flower
The Look: Goldie actually wasn't around to accept her Oscar because she was busy filming a movie in London, but she showed up the next year looking next-level incredible with a flower atop her head and eyelashes that rival Bambi's.
Jane Fonda
The Year: 1972
The Win: Best Actress, Klute
The Look: Pro tip, always pair your shaggy mullet with an Yves Saint Laurent haute couture suit and purple turtleneck if you wanna get lucky.
Faye Dunaway
The Year: 1977
The Win: Best Actress, Network
The Look: This Geoffrey Beene belted dress goes perfectly with Faye Dunaway's expression of "yeah, you better believe I just did the damn thing."
Diane Keaton
The Year: 1978
The Win: Best Actress, Annie Hall
The Look: Is this Ruth Morley blazer and skirt combo the most Diane Keaton-y outfit Diane Keaton has ever worn? I'm thinking yes.
Maggie Smith
The Year: 1979
The Win: Best Supporting Actress, California Suite
The Look: Listen, I'm into Maggie Smith's dress and all, but I'm really here to discuss literally everything about Brooke Shields' whole lewk.
Meryl Streep
The Year: 1980
The Win: Best Supporting Actress, Kramer vs. Kramer
The Look: Excuse me, but how is society not constantly obsessing over the fact that Meryl Streep wore a popped collar when she won her first Oscar? French designer Pauline Trigère nailed it.
Jessica Lange
The Year: 1983
The Win: Best Supporting Actress, Tootsie
The Look: Jessica Lange looks like the Statue of Liberty in this Valentino dress, and I, for one, am here for it.
Anjelica Huston
The Year: 1986
The Win: Best Supporting Actress, Prizzi's Honour
The Look: Oh, this ol' thing? Just an explosion of '80s asymmetrical goodness by Tzetzi Ganev, the vibes of which I'll be attempting to recreate this holiday season.
Jodie Foster
The Year: 1989
The Win: Best Actress, The Accused
The Look: A periwinkle off-the-rack dress that your mom probably wore to prom. Also, ARE THOSE NUDE STOCKINGS?
Emma Thompson
The Year: 1993
The Win: Best Actress, Howards End
The Look: Emma wore this cute Caroline Charles gown, and apparently Valentino claimed she'd "settled" by not picking a couture designer. Please give me a moment while my eyes un-roll from my head, thx.
Marisa Tomei
The Year: 1993
The Win: Best Supporting Actress, My Cousin Vinny
The Look: No one expected Marisa to take home the win, but she stole the spotlight in a Chanel gown with black piping and full-length gloves—which had kinda similar vibes to Julia Roberts' Valentino Oscars dress (coming up in a few).
Holly Hunter
The Year: 1994
The Win: Best Actress, The Piano
The Dress: Holly Hunter's dress is as classically Vera Wang as it gets, and I want it in my wardrobe ASAP in case anyone's feeling generous.
Susan Sarandon
The Year: 1996
The Win: Best Actress, Dead Man Walking
The Look: Wow, this is...a lot! For reasons that remain confusing more than 20 years later, Susan Sarandon paired her bronze Dolce & Gabbana ballgown with a bronze shawl, bronze hair, and bronze rimmed sunglasses. Okay!
Juliette Binoche
The Year: 1997
The Win: Best Supporting Actress, The English Patient
The Look: Attention @ The Academy. If I ever win an Oscar, I, too, will show up looking like a cross between the evil queen in Snow White and any given vampire. Thanks for your time.
Helen Hunt
The Year: 1998
The Win: Best Actress, As Good as It Gets
The Look: Not sure how I feel about the match-y shoes, but Helen Hunt's ice blue Tom Ford for Gucci gown holds TF up.
Kim Basinger
The Year: 1998
The Win: Best Supporting Actress, L.A. Confidential
The Look: Things I would happily wear to work if people would LET ME: this mint-green Escada gown.
Gwyneth Paltrow
The Year: 1999
The Win: Best Actress, Shakespeare in Love
The Look: Love it or hate it, Gwyneth Paltrow's baby pink Ralph Lauren princess gown is maybe the most recognizable Oscars dress of all time. Other than the dress she wore the next year with no bra, of course.
Angelina Jolie
The Year: 2000
The Win: Best Supporting Actress, Girl, Interrupted
The Look: Speaking of people looking like vampires, allow me to present Angelina Jolie in this floor-length gown by Versace. Would happily let her suck my blood.
Hilary Swank
The Year: 2000
The Win: Best Actress, Boys Don't Cry
The Look: I mean, this Randolph Duke ballgown isn't the best dress of all time, but it accomplished its job of showing off that truly massive diamond necklace.
Julia Roberts
The Year: 2001
The Win: Best Actress, Erin Brockovich
The Dress: Julia chose to wear a 1992 Valentino couture dress to take home her win, and she's saving it for her daughter Hazel. "It’s under my bed, in a box," she told People. "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 Hazel?'"
Halle Berry
The Year: 2002
The Win: Best Actress, Monster's Ball
The Look: Does anyone else remember watching Halle Berry take the stage for her historic Oscars win? She could have worn literally anything and looked amazing, but this Elie Saab gown was a glorious choice.
Jennifer Connelly
The Year: 2002
The Win: Best Supporting Actress, A Beautiful Mind
The Look: Like, would I have paired my nude Balenciaga dress with a skinny yellow scarf? No. But do I have an Oscar? Also no.
Catherine Zeta-Jones
The Year: 2003
The Win: Best Supporting Actress, Chicago
The Look: Catherine Zeta-Jones was nine (NINE!) months pregnant at the Oscars, and wow, Versace came through with her maternity dress.
Nicole Kidman
The Year: 2003
The Win: Best Actress, The Hours
The Look: Nicole Kidman's Grace Kelly vibes are so strong in this Jean Paul Gaultier dress, I'm now convinced time travel is real.
Charlize Theron
The Year: 2004
The Win: Best Actress, Monster
The Look: The pose, the Old Hollywood waves, the sparkles, the Gucci gown, the shoes. Everything about this photo screams I! AM! A! MOVIE! STAR!
Renée Zellweger
The Year: 2004
The Win: Best Supporting Actress, Cold Mountain
The Dress: Hello and welcome to Renée Zellweger's bow, courtesy of Carolina Herrera. According to the designer, "She had just finished the second Bridget Jones movie, so I took advantage of her being a little curvier than usual. Thankfully Renée loves fittings, because nothing matters more than a perfect fit, especially with a strapless... I copied the bow in my bridal line and it was one of the best-selling wedding gowns I've ever done."
Cate Blanchett
The Year: 2005
The Win: Best Supporting Actress, The Aviator
The Gown: Yellow is always a refreshing color to see on the red carpet, and this Valentino gown—paired with that red lip!—killed it.
Reese Witherspoon
The Year: 2006
The Win: Best Actress, Walk the Line
The Look: There's a reason Reese's gown looks so classic and timeless. It's vintage Dior from 1955, and is, frankly, what fashion dreams are made of.
Rachel Weisz
The Year: 2006
The Win: Best Supporting Actress, The Constant Gardener
The Look: Rachel was seven months pregnant when she won her Oscar, and turned to designer Narciso Rodriguez to create the perfect gown to accessorize her bump in what she called a "surreal"moment on the carpet.
Jennifer Hudson
The Year: 2007
The Win: Best Supporting Actress, Dreamgirls
The Look: Very into the fact that Jennifer Hudson dressed to complement the Oscar she clearly knew she was about to win. Props to Oscar de la Renta for this genius.
Marion Cotillard
The Year: 2008
The Win: Best Actress, La Vie en Rose
The Look: Forever screaming at how perfect this mermaid dress—with literal fabric scales!—is on Marion. According to designer Jean Paul Gaultier, she "initially requested something simple, but I wanted everyone to see the woman I saw."
Penélope Cruz
The Year: 2009
The Win: Best Supporting Actress, Vicky Cristina Barcelona
The Look: Penélope pulled a Reese Witherspoon and wore a vintage Balmain ballgown from 1950. As Tim Gunn noted, “It’s really a museum piece.”
Kate Winslet
The Year: 2009
The Win: Best Actress, The Reader
The Look: Kate paired her Atelier Yves Saint Laurent by Stefano Pilati dress with Grace Kelly's signature hair, and honestly, yes please.
Mo'Nique: 2010
The Year: 2010
The Win: Best Supporting Actress, Precious
The Look: Loving this regal blue color on Mo'Nique, who was dressed by Tadashi Shoji. She paired the gown with white gardenias in honor of Hattie McDaniel, the first African-American actress to win an Oscar.
Sandra Bullock
The Year: 2010
The Win: Best Actress, The Blind Side
The Look: I'd describe this one as "Disco ball but make it a Marchesa Oscar gown."
Natalie Portman
The Year: 2011
The Win: Best Actress, Black Swan
The Designer: Natalie Portman worked with Rodarte on her Oscars dress, which makes perfect sense—the designer sisters created the costumes for Black Swan, including Natalie's stunning feather-y tutu.
Octavia Spencer
The Year: 2012
The Win: Best Supporting Actress, The Help
The Dress: Like Charlize, this is just one of those dresses (by Tadashi Shoji, FYI) that just screams I AM RED CARPET ROYALTY. Also shoutout to whatever that lady in the background is doing with her legs here.
Anne Hathaway
The Year: 2013
The Win: Best Supporting Actress, Les Misérables
The Look: This dress caused so. much. drama. Basically, Anne was supposed to wear a Valentino gown to the Oscars, and the brand released a statement claiming as much before she walked the carpet. But then Anne showed up in Prada because she heard another actress was wearing a similar look, so she ended up having to issue a public apology. Hate when that happens.
Jennifer Lawrence
The Year: 2013
The Win: Best Actress, Silver Linings Playbook
The Dress: Dior, naturally. AKA the gown J.Law tripped and fell up the stairs in.
Lupita Nyong'o
The Year: 2014
The Win: Best Supporting Actress, 12 Years a Slave
The Look: Lupita chose the color of this Prada dress because "it's a blue that reminds me of Nairobi, so I wanted to have a little bit of home." She paired the gown with a Fred Leighton headband and it was *chef's kiss* perfection.
Alicia Vikander
The Year: 2016
The Win: Best Supporting Actress, The Danish Girl
The Look: Another glorious buttercup yellow moment on the red carpet, this time courtesy of Louis Vuitton and a whole lotta sparkles.
Brie Larson
The Year: 2016
The Win: Best Actress, Room
The Look: Gucci + Ruffles + a big belt = Oscar dress perfection.
Emma Stone
The Year: 2017
The Win: Best Actress, La La Land
The Dress: Emma looked like Old Hollywood royalty in this Givenchy Haute Couture dress by Riccardo Tisci, which was gorgeously fringed and made everyone immediately want to become a flapper.
Viola Davis
The Year: 2017
The Win: Best Supporting Actress, Fences
The Look: How to make a statement on the red carpet. Step One: Wear a hot red dress by Armani Privé. Step Two: Be Viola Davis.
Regina King
The Year: 2019
The Win: Best Supporting Actress, If Beale Street Could Talk
The Look: Regina King sees Angelina Jolie's famous Oscars leg slit, and would like to raise it approximately 4 inches with the help of Oscar de la Renta.
Ruth E. Carter
The Year: 2019
The Win: Best Costume Design, Black Panther
The Look: Ruth's blue, metallic gown and beaded necklace absolutely popped at the 2019 ceremony. The veteran designer has been behind the looks from so many fantastic movies, so this Oscar gold was long overdue.
Laura Dern
The Year: 2020
The Win: Best Supporting Actress, Marriage Story
The Look: We all know that the Supporting categories usually steal the whole show. Laura earned her first Oscar as family lawyer Nora Fanshaw, and arrived at the ceremony in a pink custom Armani Privé gown, embellished with gorgeous black tassels, embroiderey, and crystals.
Chloé Zhao
The Year: 2021
The Win: Best Director/Best Picture, Nomadland
The Look: Wearing a nude Hermés dress paired with crisp white sneakers, Chloé is glowing at the 93rd Academy Awards, where her film Nomadland was the big winner of the night.
Jamie Lee Curtis
The Year: 2023
The Win: Best Supporting Actress, Everything Everywhere All at Once
The Look: Wow, what a silhouette! Jamie's crystal-covered Dolce & Gabbana gown was timelessly glamorous.
Da’Vine Joy Randolph
The Year: 2024
The Win: Best Supporting Actress, The Holdovers
The Look: Da’Vine Joy won her much-deserved Oscar in a pale blue custom Louis Vuitton gown with gorgeous puffy sleeves and a long train. It was the first Oscars she has attended, and likely won’t be the last.
Robert Downey Jr.
The Year: 2024
The Win: Best Supporting Actor, Oppenheimer
The Look: Robert was one of the best-dressed male stars of the night by a country mile with his black Saint Laurent suit, paired with a unique bolo tie, and great wide-legged high-waisted trousers.
Justine Triet
The Year: 2024
The Win: Best Original Screenplay, Anatomy of a Fall
The Look: Justine, who won the Best Screenplay award for the excellent legal thriller she wrote with her partner and co-writer Arthur Harari, wore a chic embroidered custom Louis Vuitton suit over a satin top.
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