The 50 Most Iconic Oscar Dresses of All Time

From Old Hollywood frocks to modern couture.

The Oscars have forever been the fashion Olympics for Hollywood's brightest stars. Style chameleons like Cate Blanchett and Nicole Kidman regularly steal the show, while risky contenders like Björk still live in our hearts (and memes). Ahead, the most iconic red carpet looks in Academy Awards history that despite the push for #AskHerMore make us actually crave the answer to "Who are you wearing?"

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Grace Kelly, 1955

The queen (princess?) of red carpet elegance, Grace Kelly wearing this mint-green spaghetti strap number is everything. 

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Audrey Hepburn, 1968

The definition of classic beauty is Audrey Hepburn wearing this modern lace-up dress with strategic cutouts (mostly because we're still dying to wear it today).

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Natalie Wood, 1968

When Natalie Wood stole the show in a sparkly dress, big earrings, a giant hair bow, and perfect *double* cat-eye wings. 

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Barbra Streisand, 1969

Not one to wear anything close to traditional, here's Babs wearing a sparkly pantsuit sealed with a bow (and the perfect rounded bob to match). 

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Elizabeth Taylor, 1970

Elizabeth Taylor wears a plunging custom violet chiffon dress designed by Edith Head to showcase a pear-shaped diamond from her husband Richard Burton. 

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Goldie Hawn, 1971

Goldie Hawn matches her florals with a "flower child"-style  spaghetti strap dress and a darling updo. 

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Cher, 1973

Cher shows off her toned abs in a sequined belly dancer get-up that led the way for midriff-baring stars like Britney Spears. 

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Lauren Hutton, 1975

This is how you have fun on the red carpet, as demonstrated by Lauren Hutton wearing a rainbow dress topped with a fur chubby jacket. 

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Jacqueline Bisset, 1976

Making a case for the one-shouldered trend to come, Jacqueline Bisset wore this non-traditional striped gown with a high neck.  

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Diana Ross, 1982

In which Diana Ross brought the glam factor with a red sparkly key-hole dress and a larger-than-life white boa. 

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Cher, 1986

A look that was one-of-a-kind (because, c'mon, it's Cher) and groundbreaking for its time, it has rarely repeated itself on the Oscars red carpet (but see the Grammys red carpet for the many ways her bravado has influenced modern over-the-top fashion).  

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Geena Davis, 1991

Looking like a golden statuette, Geena Davis wears a beautiful off-the-shoulder golden brocade gown. 

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Cindy Crawford, 1991

The ultimate Kim Kardashian move: show up at the Oscars (not nominated) and steal all the attention. (This might be the most va-va-voom Oscars dress in history, for what it's worth). 

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Kate Winslet,1996

Color at the Oscars often speaks for itself, and this bright pink gown (paired with an equally vibrant red wrap) spoke *volumes*, channeling old-school glamour. 

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Salma Hayek, 1997

At Salma Hayek's first Oscars, she appeared wearing a super-shimmery Armani gown and a tiara (the best way to make a first impression, no?). 

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Courtney Love, 1997

Courtney Love looks boudoir-elegant (and decidedly un-grunge-y) in this silky '90s slip dress from Versace. 

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Nicole Kidman, 1997

Considered one of the most influential red carpet gowns in fashion history, Nicole Kidman's silk chartreuse gown by newly minted Dior designer John Galliano helped to put him on the map and is considered the first true "couture" gown on the red carpet. 

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Celine Dion, 1999

Not about to show up to the Oscars in a boring floor-length gown, Celine Dion showed up in this backwards tuxedo from Christian Dior instead (with the matching white fedora to match).

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Gwyneth Paltrow, 1999

1999 was the year Gwyneth made pastel pink her domain in this Ralph Lauren gown (she's worn the color numerous times since). She nabbed the Best Actress Award for Shakespeare in Love in it, too, so consider it lucky. 

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Renée Zellweger, 2001

Renée Zellweger making lemon meringue look divine in a vintage chiffon dress by Jean Dessès.

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Julia Roberts, 2001

Our favorite all-American sweetheart looked flawless in this vintage Valentino work of art from 1982, where she took home a win for her portrayal of Erin Brockovich.

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Björk, 2001

Several years later, the Icelandic singer is now infamous for this swan dress designed by Marjan Pejoski.

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Halle Berry, 2002

One of our favorite Oscar looks of all time, Berry oozed elegance in this embroidered burgundy Elie Saab dress with a satin train and her signature pixie cut. That night, she was the first black woman to take home a best actress award for Monster's Ball.

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Jennifer Lopez, 2003

It feels like J.Lo was born knowing how to nail an entrance. Case in point: this mint green one-sleeve, asymmetrical cape dress that made her skin look radiant (just one of many red carpet knockouts). 

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Charlize Theron, 2004

This sleek crystal Gucci gown with a backless cut, draping train, and '40s pin curls looked beyond stunning on the South African beauty, who nabbed the Best Actress award for her role in Monster that year.

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Uma Thurman, 2004

The Kill Bill actress broke the mold in this Christian Lacroix gown with a silk-wrap waist and cropped sleeves.

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Cate Blanchett, 2005

Eternal style chameleon Cate Blanchett took home an award for her role as Katherine Hepburn in The Aviator this year, but her accolades started earlier in the evening when she appeared in this yellow taffeta one-shoulder Valentino gown that's still considered one of the best Oscars gowns in history

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Hilary Swank, 2005

The Oscar winner for Million Dollar Baby stole the show in this conservative, yet daring, navy Guy Laroche gown with a super low back.

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Michelle Williams, 2006

Cementing her status as a red carpet icon, Williams paired a bright red lip and soft up-do with this lovely mustard Vera Wang gown.

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Keira Knightley, 2006

The actress topped 2006 best-dressed lists in an aubergine taffeta gown, custom-made by Vera Wang.

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