OSCARS 2021

The 30 Most Memorable Oscar Dresses of All Time

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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 recently warned, 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 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, 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.” Here, the 30 most memorable gowns of all time.

1
Charlize Theron
Photo by Neilson Barnard/Getty Images

Theron hit the red carpet at the 2019 in a backless, periwinkle Dior gown—and brunette bob.

2
Constance Wu
Photo by Steve Granitz/WireImage

Wu gave Belle realness in this Versace gown at the 2019 Oscars.

3
Rita Moreno

In 2018, Moreno walked the Oscars red carpet in the same black and gold gown she wore to the Oscars in 1962.

4
Lady Gaga
Photo by Kevin Mazur/WireImage

The Azzedine Alaïa dress—and gloves—that inspired a thousand memes in 2015.

5
Zendaya
Photo by Jeff Kravitz/FilmMagic

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.

6
Jennifer Lawrence
Photo by Jason Merritt/Getty Images

In Dior at the 2013 awards show.

7
Lupita Nyong’o

The Us actress wore Prada at the 86th Annual Academy Awards in 2014.

8
Meryl Streep
Photo by Gregg DeGuire/FilmMagic

In jaw-dropping Lanvin at the 2012 Oscars.

9
Gwyneth Paltrow

At the 84th Annual Academy Awards in 2012 wearing a Tom Ford cape.

10
Angelina Jolie

Wearing Atelier Versace at the 84th Annual Academy Awards in 2012.

11
Jennifer Lawrence

Lawrence at the 83rd Annual Academy Awards in 2011 wearing a red Calvin Klein Collection dress.

12
Penelope Cruz

The actress chose an Atelier Versace gown for the 79th Annual Academy Awards in 2007.

13
Marion Cotillard

The French actress stunned at the 80th Annual Academy Awards in 2008 wearing Jean Paul Gaultier couture.

14
Hilary Swank

Swank at the 77th Annual Academy Awards in 2005 wearing backless Guy Laroche.

15
Diane Keaton

At the 76th Annual Academy Awards wearing a three-piece menswear-inspired suit with bowler hat.

16
Jennifer Lopez

Lopez during the 75th Annual Academy Awards in 2003, donning an unexpected mint hue.

17
Halle Berry

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.

18
Julia Roberts
Photo by William Conran - PA Images/PA Images via Getty Images

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.

19
Björk
Photo by Jeff Kravitz/FilmMagic, Inc

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.

20
Cate Blanchett

At the 71st Annual Academy Awards in 1999 wearing a sheer John Galliano dress with an open back.

21
Gwyneth Paltrow
Photo by Jeffrey Mayer/WireImage

Wearing Ralph Lauren at the Oscars in 1999.

22
Celine Dion

Who could forget the backward Dior tuxedo at the 71st Annual Academy Awards in 1999?

23
Sharon Stone

Ever the envelope-pusher, Stone wore a Gap shirt paired with a Vera Wang skirt to the 70th Annual Academy Awards in 1998.

24
Nicole Kidman

Speaking of Galliano: At the 69th Annual Academy Awards in 1997, Kidman would forever change red carpet dressing by sporting one of his designs for Dior, a flawless, devastating silk gown in iridescent chartreuse that immediately appalled Joan Rivers and upstaged Tom Cruise.

25
Madonna

The Like a Virgin superstar wore Bob Mackie and $20 million worth of Harry Winston diamonds at the 63rd Annual Academy Awards in 1991.

26
Anjelica Huston

At the 58th Annual Academy Awards in 1986 wearing a one-sleeve emerald green dress.

27
Diana Ross
Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

Photographed here in 1982.

28
Cher

Kim Kardashian recreated this look, which Cher wore to the 45th Annual Academy Awards in 1973, for Halloween.

29
Barbra Streisand

At 41st Annual Academy Awards in 1969 wearing sequin see-through bell-bottom pants with a matching top.

30
Grace Kelly

In mint Givenchy at the 1955 Oscars, where she won Best Actress for her role in the 1954 film The Country Girl.