Finish line’s in sight! We’ve glammed up for the Golden Globes, mellowed out for the SAGs, and pulled out almost all the stops for the Grammys. But the mother of all award shows will always be the Oscars — happening tonight.
Oscars bingo is all set up, the liquor cabinet’s stocked, and we’re ready to fight someone if Parasite doesn’t win big. The brainstorming has begun for who’s going to be wearing what (Charlize Theron in Dior? Margot Robbie in Chanel? Florence Pugh in sequins and sunnies?). All we can do is wait and see. But to pass the time between now and Sunday night, we’re taking a walk down memory lane and reminiscing on the best red carpets of Oscars past. It’s one of our favorite things to do leading up to the show (besides planning a themed menu and plotting a drinking game). While style trends have changed through the years, the extravagance, the luxury that comes with the Academy Awards is steadfast.
In anticipation of our favorite red carpet of the year, hop in the DeLorean for a peek through the history of Hollywood’s ultimate prom to see which looks have held up. Ahead, find out who made our all-time best-dressed list from Audrey Hepburn to Queen Latifah and everyone in between.
Audrey Hepburn, 1954
It never took much to make the late Audrey Hepburn look glamorous, but in this Givenchy gown, Hepburn, glowing from winning an Oscar for Roman Holiday, is nothing short of perfection.
Audrey Hepburn in Givenchy.Photo: NBCU Photo Bank/Getty Images.
Grace Kelly, 1955
Designed by arguably the most famous costumier in history, Edith Head, Grace Kelly’s Oscars look was, like most Grace Kelly looks, an absolute winner.
Grace Kelly in Edith Head. Photo: Silver Screen Collection/Hulton Archive/Getty Images.
Madonna, 1991
Arm-in-arm with Michael Jackson and dripping in Old Hollywood glamour, there’s nothing we’d rather see Madonna wearing to the 63rd Annual Academy Awards than this Bob Mackie ensemble.
Madonna in Bob Mackie.Photo: Ron Galella/WireImage/Getty Images.
Winona Ryder, 1994
Who doesn’t love a Gatsby-esque gown at the Oscars? Photo: Ron Galella Collection/Getty Images.
Elizabeth Hurley, 1995
Head-to-toe white? Sweetheart neckline? Floor-length sequins? Check! Check! Check!
Elizabeth Hurley in Versace.Photo: Jim Smeal/WireImage/Getty Images.
Winona Ryder, 1996
While we’re used to seeing 90s-era Winona Ryder donning all-black ensembles, this champagne-colored vintage gown is an unexpected, and dazzling, switch-up.
Winona Ryder in a vintage champagne gown. Photo: Jim Smeal/WireImage/Getty Images.
Courtney Love, 1997
The queen of grunge got all dolled up by Versace for the 1997 Academy Awards — and we support it 100%.
Courtney Love in Versace. Photo: Jim Smeal/WireImage/Getty Images.
Sharon Stone, 1998
We would normally advise against wearing the Gap at the Oscars— but when it’s combined with Vera Wang and draped on Sharon Stone, it’s hard not to be convinced that it’s right where it belongs.
Sharon Stone in Gap and Vera Wang.Photo: Mychal Watts/WireImage/Getty Images.
Celine Dion, 1999
A suit on the red carpet is hardly a nuanced idea in 2019, but in 1999, worn backwards of all things — let’s just say our fashion minds were blown upon seeing Celine Dion in this John Galliano set.
Celine Dion in John Galliano.Photo: SGranitz/WireImage/Getty Images.
Gwyneth Paltrow, 1999
Pretty In Pink might have starred Molly Ringwald, but Gwyneth Paltrow (that year’s Best Actress winner for Shakespeare in Love) looked the part in this bubblegum pink number by Ralph Lauren.
Gwyneth Paltrow in Ralph Lauren. Photo: Frank Trapper/Corbis/Getty Images.
Queen Latifah, 2000
Blue is definitely Queen Latifah’s color.
Queen Latifah in a blue dress. Photo: Steve Granitz/WireImage/Getty Images.
Renée Zellweger, 2001
A long way from donning PJs all day and micro-minis at work in her role as Bridget Jones, Renée Zellweger classed up for the red carpet in a vintage yellow frock by Jean Dresses.
Renée Zellweger in a vintage dress by Jean Dresses.Photo: Chris Weeks/Getty Images.
Halle Berry, 2002
A sheer gown and an Oscar? Becoming the first Black woman to win Best Actress, Halle Berry took down all the competition — both on the red carpet and the stage — in this Elie Saab frock.
Halle Berry in Elie Saab.Photo: Kevin Mazur/WireImage/Getty Images.
Charlize Theron, 2004
Has there ever been a time when Charlize Theron isn’t glowing?
Charlize Theron in Dior.Photo: Jeff Kravitz/FilmMagic/Getty Images.
Beyonce Knowles, 2005
There to perform not one, not two, but three songs, Beyonce went with a black velvet number that hugged her curves in all the right places. Thanks Atelier Versace!Beyonce Knowles in Atelier Versace. Photo: ROBYN BECK/AFP/Getty Images.
Michelle William, 2006
Accompanying her then-boyfriend, the late Heath Ledger, Michelle Williams was a shining ray of light in this yellow number by Vera Wang.
Michelle Williams in Vera Wang.Photo: Frazer Harrison/Getty Images.
Nicole Kidman, 2007
Nicole Kidman in Balenciaga would hardly be our first choice, but after seeing the Oscar-winning Australian actress in this red hot gown, we promise to never doubt the combination again.
Nicole Kidman in Balenciaga.Photo: Frazer Harrison/Getty Images.
Anne Hathaway, 2009
Is it just us, or does Anne Hathaway look like an actual Oscar in this fitted Armani Privé dress?
Anne Hathaway in Armani Prive.Photo: John Shearer/WireImage/Getty Images.
Zoe Saldana, 2010
Let’s get one thing straight: no one (and we mean no one) could pull off this dress other than Zoe Saldana.
Zoe Saldana in Givenchy Haute Couture. Photo: Bob Riha, Jr./Getty Images.
Cate Blanchett, 2011
In this lavender haute couture gown by Givenchy, Cate Blanchett wasn’t just an award-winning actress — she’s a damn fashion icon.
Cate Blanchett in Givenchy Haute Couture.
Michelle Williams, 2012
Red on the red carpet is hardly a task for the faint of heart, but Michelle Williams, nominated for her role as Marilyn Monroe in My Week With Marilyn, made it look like the easiest thing in the world thanks to one hell of a pixie cut and 300 hours of work in the Louis Vuitton Paris atelier.
Michelle Williams in Louis Vuitton.Photo: Bob Riha, Jr./Getty Images.
Angelina Jolie, 2012
No one does a high slit quite like Mrs. Smith herself, Angelina Jolie, who generated one of the greatest Oscar memes ever with this pose.
Angelina Jolie in Atelier Versace. Photo: Donato Sardella/WireImage/Getty Images.
Jennifer Lawrence, 2013
En route to accept her Oscar for Silver Linings Playbook, Jennifer Lawrence had all eyes on her in this pastel-colored Dior gown. It was pretty chill, even for her.
Jennifer Lawrence in Dior. Photo: Gregg DeGuire/WireImage/Getty Images.
Lupita Nyong’o, 2014
Lupita Nyong’o — she snagged an Oscar that night for Best Supporting Actress in 12 Years a Slave — lit up the sky in this baby blue Prada gown.
Lupita Nyong’o in Prada.Photo: Axelle/Bauer-Griffin/FilmMagic/Getty Images.
Zendaya, 2015
For an Oscars newbie, Zendaya looked anything but out of place in this Vivienne Westwood stunner of a gown.
Zendaya in Vivienne Westwood.Photo: Dan MacMedan/WireImage/Getty Images.
Sienna Miller, 2015
For his red carpet debut designing for Oscar de la Renta, Peter Copping made quite the impression with this bow-embellished, square neck gown on Sienna Miller.
Sienna Miller in Oscar de la Renta.Photo: Gregg DeGuire/WireImage/Getty Images.
Olivia Wilde, 2016
Olivia Wilde going backless in Valentino Haute Couture? We’ll take it.
Olivia Wilde in Valentino Haute Couture.Photo: Steve Granitz/WireImage/Getty Images.
Taraji P. Henson, 2017
Taraji P. Henson blew us back to the 1950s in this Alberta Ferretti Old Hollywood-esque velvet gown. And that necklace? Whew, we’re getting excited just thinking about it.
Taraji P. Henson in Alberta Ferretti. Photo: Frazer Harrison/Getty Images.
Naomie Harris, 2017
Of the four Moonlight stars dressed by Raf Simons for Calvin Klein, this white sequin frock on Naomie Harris went home with the prize (for best dressed) in our book.
Naomie Harris in Raf Simons for Calvin Klein.Photo: George Pimentel/FilmMagic/Getty Images.
Saoirse Ronan, 2018
A long way from dress shopping at a Sacramento thrift shop! This bubblegum pink frock on Lady Bird lead actress, Saoirse Ronan is one for the record books.
Saoirse Ronan in Calvin Klein By Appointment.Photo: Jeff Kravitz/FilmMagic/Getty Images.
Margot Robbie, 2018
Margot Robbie was a breath of fresh air in this showstopping white gown courtesy of Chanel.
Margot Robbie in Chanel.Photo: Neilson Barnard/Getty Images.
Gemma Chan, 2019
Hot pink came out running at the 91st Annual Academy Awards, but if you ask us, Gemma Chan won the marathon in this neon poof dress courtesy of Versace.
Gemma Chan in Versace. Photo by Frazer Harrison/Getty Images.
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