Grace Kelly
Edith Head, 1955
The soon-to-be Princess of Monaco wore this aquamarine dress to collect her Oscar for her role in “The Country Girl.” At the time, it was the most expensive Oscar dress in history; the silk alone cost $4,000. Perhaps that’s why she wore it three times: first to “The Country Girl” premiere, next to a cover shoot for Life magazine and finally, with slight alterations, to the Academy Awards. “Kelly was a very practical person who kept all of her clothes in pristine condition,” says Bronwyn Cosgrave, author of “Made for Each Other: Fashion and the Academy Awards.”
Everett Collection
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Marlene Dietrich
Christian Dior, 1951
The legendary screen siren seems ready to swipe the Oscar for Best Foreign Language Film from Italian Consul Mario Ungara, just as she stole the show earlier in the evening wth her minimalist black dress. It didn’t matter that she wasn’t even up for an award. Poured into a sexy Dior frock, Dietrich dominated fashion and gossip chatter for days.
LATS
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Nicole Kidman
Christian Dior, 1997
John Galliano’s first couture collection for Dior in January 1997 had fashionistas hailing him as a genius. It incited excitement for its tribal African and Chinoiserie themes. Nicole Kidman took this chartreuse dress straight off the catwalk to the red carpet.
Kevin Mazur/WireImage
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Angelina Jolie
Elie Saab, Lorraine Schwartz jewelry, 2009
This might be a simple dress, but it wins best supporting role for the way it made Jolie’s accessories shine. No one wears tasteful yet eye-popping, baubles like her. These emerald teardrop earrings cost $2.5 million, and proved to be worth every penny.
Kevork Djansezian/Getty Images
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Hilary Swank
Guy Laroche, 2005
Despite a lucrative contract with Calvin Klein, Swank did the unthinkable when she shocked the CK team and picked a better dress, appearing on the red carpet in a backless Laroche gown.
Steve Granitz/WireImage
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Michelle Williams
Vera Wang, 2006
This is the moment Sundance actresses took hold of the red carpet. “No one had seen this shade of yellow, and I don’t believe anyone beyond the film industry cognoscenti knew who she was,” says Cosgrave. “She used her indie power in a subtle and tasteful way. These actresses had supermodel beautiful looks and incredible talent and are not afraid to use their beauty.”
Frazer Harrison/Getty Images
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Hailee Steinfeld
Marchesa, 2011
How does a teenager dress for the Oscars? With a little help from the Weinstein Co.’s first lady and Marchesa designer Georgina Chapman. Steinfeld went fairy-tale Marchesa and pulled off sweet but not saccharine. (Only a young girl can get away with looking like a princess. Take note, Gwyneth.)
Steve Granitz/WireImage
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Julia Roberts
Valentino, 2001
When Tinseltown’s biggest star dons a secondhand dress—from the designer’s 1992 haute couture collection — the world follows suit. Women everywhere started to pillage used clothing stores and scour their mom’s attics. Steele eventually put the frock on display
at FIT.
Kevin Winter/Getty Images
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Elizabeth Taylor
Edith Head, 1969
Taylor often chose her jewels first and had dresses designed around them. In this case, she commissioned Head to make a dress matching her violet eyes. To. Match. Her. Eyes. On her arm was Richard Burton, the ultimate Oscar-goddess accessory. The periwinkle gown fetched $167,500 at auction in 1999.
Courtesy of AMPAS
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Faye Dunaway
Theadora van Runkle, 1968
This was one of the last times a studio costumier had a mega moment at the ceremony before ceding control of the red carpet completely to fashion designers.
Courtesy of AMPAS
