Best and worst Oscars dresses of all time

Brie Larson attends the 89th Annual Academy Awards on Feb. 26, 2017. Kevork Djansezian/Getty Images

There was a time, long ago, when the Oscars weren’t the be-all and end-all of red carpet fashion events. These were the days before celebrity stylists and glam squads, when the stars chose their own dresses or at the most, turned to their favourite designer for a special creation.

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While this left a lot more room for error — and refreshingly daring looks — it also more clearly highlighted each individual actress’s personal style. For every chic Givenchy creation that Audrey Hepburn wore (she had a close relationship with the designer), there was a boundary-pushing look worn by Cher or a glam statement from Diana Ross. All of which spoke directly to their individual personalities.

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“Actors [were] more in control of their wardrobes,” Bridget Foley, executive editor of Women’s Wear Daily, said to Vanity Fair. “Ironically, the result was more diversity because what celebrities wore more accurately reflected their personalities and senses of style than we see today. Someone with a casual sense of style might dress casually; someone who wanted to have fun and/or become a topic of sartorial conversation would dress for the intent.”

Of course, there are stars who take risks today — Tilda Swinton’s cerebral choices, and the edgy and age-appropriate looks worn by ingenues like Zendaya and Janelle Monae immediately pop to mind — but one can’t help to think that the overarching perfection of it all, from high-def contouring to whimsical nail art, makes it a less than thrilling affair.

READ MORE: Oscars 2018 predictions: Picks for this year’s Academy Award winners

On the heels of the 2018 Oscars, we take a look at the best and worst (but those are kind of the best, too) Oscars red carpet looks of all time.

Be sure to come back to for full coverage of the 2018 Oscars on Sunday, March 4.

Best dresses

Grace Kelly in Edith Head, 1955

Sunset Boulevard/Corbis via Getty Images

Faye Dunaway in Theadora Van Runkle, 1968

Bettmann / Contributor

Audrey Hepburn in Givenchy, 1975

Ron Galella/WireImage

Lauren Hutton in Halston, 1975

Michael Montfort/Michael Ochs Archives/Getty Images

Debbie Allen, 1982

Archives/ABC via Getty Images

Diana Ross, 1982

Michael Montfort/Michael Ochs Archives/Getty Images

Gwyneth Paltrow in Calvin Klein, 1996

Mirek Towski/DMI/The LIFE Picture Collection/Getty Images

Sharon Stone in a Vera Wang skirt, 1998

Kevin Mazur/WireImage

Michelle Williams in Vera Wang, 2006

Frank Trapper/Corbis via Getty Images

Lupita Nyong’o in Prada, 2013

Rick Rowell/ABC via Getty Images

Worst dresses

Bette Davis, 1955Barbara Streisand in Arnold Scaasi, 1969. Getty Images
Ron Galella/WireImage

Cher in Bob Mackie, 1973

Ron Galella/WireImage

Elizabeth Taylor in Valentino, 1993

Jim Smeal/WireImage

Whoopie Goldberg, 1993

Barry King / Contributor

Kate Winslet in Alexander McQueen, 1998

Frank Trapper/Corbis via Getty Images

Faith Hill in Versace, 2002

Steve Granitz/WireImage

Diane Keaton in Ralph Lauren, 2004

Gregg DeGuire/WireImage

Sarah Jessica Parker in Chanel, 2010

Jeff Kravitz/FilmMagic

Heidi Klum in Marchesa, 2016

C Flanigan/FilmMagic


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