red carpet derby

The 20 Most Memorable Oscars Looks of All Time

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Something tells me that this time next year, after the Oscars this Sunday, we’ll update this list with some harnesses and a very large dress courtesy of Lady Gaga. But the Oscars have long been a source of red-carpet inspiration. Yes, every once in a while there’s a nugget of sartorial gold. From the Cinderella-esque dresses worn by Grace Kelly and Lupita Nyong’o, to the wackier outfits from Cher and Björk, this particular red carpet has seen a lot. Scroll to see memorable dresses that made headlines over the years and caught our fashion editors’ attention.

Audrey Hepburn in Givenchy, 1954

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Audrey Hepburn’s 40-year friendship and professional partnership with Hubert de Givenchy began the night she won Best Actress for her role in Roman Holiday. The white floral Givenchy dress was the first of his she’d ever worn.

Grace Kelly in Edith Head, 1955, With Edmond O’Brien

Photo: Sunset Boulevard/Corbis via Getty Images

Kelly wore a blue satin gown by the legendary costume designer Edith Head and took home the Best Actress Award for The Country Girl. One year later, she married Prince Rainier III and became Princess of Monaco.

Barbra Streisand in Arnold Scaasi, 1969, With Jack Albertson and Anthony Harvey

Photo: ABC Photo Archives/ABC Photo Archives/Getty Images

Streisand’s 1969 Oscars night was very eventful. Not only did she tie (yes, tie!) for Best Actress with Katharine Hepburn, but according to Vanity Fair, Streisand didn’t realize her outfit was sheer until she went onstage to accept the Best Actress Award for Funny Girl. Under the harsh lights, the sparkly jumpsuit became transparent. But it’s a good look!

Dionne Warwick (Designer Unnamed) in 1972 With Her Husband, William Elliott, and Sister, Dee Dee

Photo: Fotos International/Getty Images

We may not know a lot about this ornate satin tux, but it still deserves all the praise. Also, how sweet is she for taking her sister as her guest?

Diane Keaton in Ruth Morley, 1978

Photo: Ron Galella/WireImage

Diane Keaton is known for her glorious menswear style, so much so that it inspired her character’s wardrobe in Annie Hall. According to Ellethe film’s costume designer didn’t love the idea of Keaton wearing her own clothes in the film, but Woody Allen insisted. The film inspired a generation of women to dress like her. Keaton paid homage to the character here when picking up an Academy Award for her role in a Ruth Morley multilayered skirt, blazer, flower broach, and scarf.

Farrah Fawcett in Stephen Burrow, 1978, With Marcello Mastroianni

Photo: ABC Photo Archives/Getty Images

Dressing like a human Oscars statue never goes out of style.

Cher in Bob Mackie, 1986

One of the craziest Oscars looks of all time, Cher’s unforgettable beaded dress and headdress became even more iconic after RuPaul’s Snatch Game. Despite the outfit’s lasting power, today Cher apparently regrets it. “I knew some people in the Academy didn’t think that I was a serious actress,” she told Vogue. “I always felt a bit sad that I presented Don Ameche with his Best Supporting Actor Award in that outfit. It seemed to make him a little nervous.”

Madonna in Bob Mackie, 1991, With Michael Jackson

Photo: Ron Galella/WireImage

A look so good, the Kardashians copied it. Madonna and Michael Jackson arrived at the 1991 Academy Awards arm in arm. Madonna later stole the entire Oscars show with a rendition of Stephen Sondheim’s “Sooner or Later (I Always Get My Man).”

Sharon Stone in the Gap and Vera Wang, 1998, With Phil Bronstein

Photo: Mychal Watts/WireImage

Sharon Stone has never shied away from a good Gap top. After wearing a Gap turtleneck to the 1996 awards, she returned two years later in a Gap men’s button down and a satin Vera Wang skirt.

Celine Dion in John Galliano, 1999

Photo: SGranitz/WireImage

Was 1999 the best Oscars ever? If you’re looking just at the red carpet, probably. Dion flipped the fashion script by literally flipping this Dior tuxedo around, and wearing it backwards.

Björk in Marjan Pejoski, 2001

Photo: Mirek Towski/FilmMagic

Perhaps the the most memorable, craziest Oscars look of all time, Björk’s infamous swan dress is legendary. She was nominated for Best Original Song for “I’ve Seen it All” from Dancer in the Dark, which she also starred in.

Halle Berry in Elie Saab, 2002

Photo: KMazur/WireImage

Berry wore this artfully embroidered sheer Elie Saab gown when she became the first (and still only) black woman to win Best Actress for her role in Monster’s Ball. The dress had “fashion critics raving for days,” according to Variety.

Gwyneth Paltrow in Alexander McQueen, 2002

Photo: SGranitz/WireImage

A #freethenipple moment years before the hashtag went viral, Paltrow’s sheer top and full skirt were apparently all the rage. In a Goop post from 2013, GP admitted that while she “still love[s] the dress itself,” she “should have worn a bra” and styled the look differently.

Jennifer Lopez in Valentino, 2003

Photo: J. Vespa/WireImage

This look is so early 2000s: Not only did J.Lo arrive to the Academy Awards with her then-boyfriend Ben Affleck, but her frosted green eyelids and low bun really cemented the time period. The dress, however, came from another era, inspired by a Valentino look worn by Jackie O in 1967.

Anne Hathaway in Armani Prive, 2009

Photo: Steve Granitz/WireImage

Hathaway may have lost the Best Actress award to Kate Winslet, but she still got to shine onstage during an opening number with host Hugh Jackman, and she stole the red carpet in this glittery gown.

Zoe Saldana in Givenchy, 2010

Photo: Brian To/WireImage

The dress has it all: sparkles, an absurd amount of tulle, and ombré purple. Over-the-top details make it work.

Jennifer Lawrence in Calvin Klein, 2012

Photo: Jeffrey Mayer/WireImage

This was J.Law’s Oscars debut, for her role in Winter’s Bone, as well as the world’s first introduction to the actress. Part Bay Watch, part simple ’70s glamour (with Farrah Fawcett–esque hair), the dress showed that Lawrence was one to watch.

Angelina Jolie in Atelier Versace, 2012

Photo: Ethan Miller/Getty Images

The leg that broke the internet. Jolie’s pose went viral overnight and even received its own Twitter handle, @AngiesRightLeg. The Cut’s photo editors Photoshopped her leg on everyone else there. Internet chaos aside, the velvet Versace gown was a win.

Lupita Nyong’o in Prada, 2014

Photo: Axelle/Bauer-Griffin/FilmMagic

Nyong’o won Best Supporting Actress for her role in 12 Years a Slave wearing this Cinderella-esque look.

Janelle Monáe in Elie Saab, 2017

Photo: Steve Granitz/WireImage

Two years ago, Monáe had quite the Oscars night with her roles in Moonlight and Hidden Figures. On top of that, she stole the red carpet in a dress straight out of a couture fairy-tale with a matching golden crown.

Agnès Varda in Gucci, 2018

Photo: Steve Granitz/WireImage/Getty Images

At a black-tie event, sometimes the best statement is a slouchy loungewear set, complete with cardigan. Agnès Varda may not be a millennial, but she sure can rock a full Gucci look.

The 20 Most Memorable Oscars Looks of All Time