The Stories Behind The Most Famous Oscars Looks

From Audrey Hepburn to Angelina Jolie, we look back at Hollywood's greatest sartorial highlights.
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From glamorous gowns to statement frocks, every Academy Awards dress is chosen with purpose and intent. These are the stories behind some of the most significant looks from all 95 years of the Oscars.

Bette Davis (1936)

After being initially overlooked for the previous year’s award, Bette Davis was finally acknowledged by the Academy and chose to make a visual statement in what would be the first example of “protest dressing”. She arrived “unsuitably gowned” in Orry-Kelly intending to look like something “the hired help” would wear.

Bette Davis
Bette Davis and Canadian-born film producer Jack L. Warner (one of the founders of Warner Bros. Pictures) hold Davis’s Oscar for Best Actress in a Leading Role. (Credit: Image: Getty)

Hattie McDaniel (1940)

Winner of Best Supporting Actress and the first African-American to receive an Oscar, McDaniel was forced to enter the “whites only” hotel by a different door and sit at a segregated table. McDaniel stood proudly for all African-Americans with gardenias (said to be a symbol of purity) on the turquoise beaded jacket that matched her gown. Hollywood columnist Louella Parsons described her as “up to the queen’s taste” as she delivered a heartfelt acceptance speech to rapturous applause.

Hattie McDonald
Actress Fay Bainter (right) presenting Hattie McDaniel (left) her award for her supporting role in Gone With the Wind. (Credit: Image: Getty)

Audrey Hepburn (1955)

Performing Ondine on Broadway on the evening of the awards, Audrey Hepburn was rushed across town with a police escort just in time to accept the Oscar for Best Actress. The fit-and-flare shape and open back of her deceptively simple lace organdie dress were designed to frame her fine upper features and shapely shoulders, while the flowing skirt softened her strong dancer’s legs and diminished what she called her “big feet”. It was the first time she’d been seen in a dress by Hubert de Givenchy, and so began their devoted friendship and collaboration, which marked the beginning of the designer/celebrity affiliation.

Audrey Hepburn
Audrey Hepburn, wearing a Givenchy gown, surrounded by journalists after winning her Best Actress Oscar at the ceremony in New York City. (Credit: Image: Getty)

Julie Christie (1966)

The first woman to wear pants to accept an Oscar, Christie and a friend made her gold lamé jumpsuit from a commercial pattern. The homemade outfit encapsulated the Youthquake movement, appealing to a young American audience poised to reject a conformist society. Time magazine would go on to state that as a symbol of her generation, Christie was more influential than the “ten best-dressed women combined”.

Julie Chirstie
Actress Julie Christie kisses the Best Actress Oscar she won at the 38th Annual Academy Awards for her performance in the movie Darling. (Credit: Image: Getty)

Sacheen Littlefeather (1973)

Marlon Brando won Best Actor for a second time and asked Apache/Yaqui actor Sacheen Littlefeather (also known as Marie Cruz) to reject it on his behalf. She mounted the stage in a genuine Apache buckskin dress to demonstrate against the clichéd “treatment of American Indians … by the film industry”.

Sacheen Littlefeather
Sacheen Littlefeather holds a written statement from actor Marlon Brando refusing his Best Actor Oscar on stage at the Academy Awards. (Credit: Image: Getty)

Cher (1986)

Cher’s red-carpet style had always been highly anticipated, but this revealing punk-meets-showgirl creation by Bob Mackie topped them all. Deeply disappointed the Academy had not acknowledged her performance in Mask, Cher wanted to prove she still had it at 40, and instructed Mackie to go wild with a design that would make her impossible to ignore. Having stolen the spotlight, Cher eclipsed every other star at the ceremony and her ensemble continues to be regarded as one of the most iconic Oscar outfits of all time.

Cher at the Dorothy Chandler Pavillion in Los Angeles for the 58th Academy Awards. (Credit: Image: Getty)

Sharon Stone (1998)

Sharon Stone (pictured with then-husband Phil Bronstein) wrote her own rules on red-carpet fashion, wearing a satin Vera Wang skirt with a simple white button-down Gap shirt. The unorthodox pairing redefined modern glamour, making it more attainable, and catapulted the classic white shirt to the forefront of fashion must-haves.

Sharon Stone
Sharon Stone & Phil Bronstein at the 1998 Academy Awards in Los Angeles. (Credit: Image: Getty)

Gwyneth Paltrow (1999)

The winner of the Best Actress Oscar, Gwyneth Paltrow epitomised the all-American sweetheart in a taffeta ball gown by the foremost fashion purveyor of instant American classics, Ralph Lauren. The dress arrived slightly too big and Paltrow was slammed by the media for her fashion faux pas, but it only served to enhance the image of a delicate, youthful actress humbled to have made a big splash in Hollywood.

Gwyneth Paltrow
Gwyneth Paltrow at the 71st Annual Academy Awards. (Credit: Image: Getty)

Anne Hathaway (2009)

Through this decade there was one woman who revolutionised the modern red carpet: Rachel Zoe. The LA stylist had become a celebrity in her own right, building her brand with a television show and an army of online devotees. She was responsible for many A-listers’ looks, including Best Actress nominee Anne Hathaway’s custom Giorgio Armani champagne column gown. Inspired by “Shanghai in the ’30s” and merging screen siren with sea siren, it was lined in Swarovski crystals, the round paillettes shimmering with pearly iridescence and graduating from tiny circles that increased in size as they spiralled diagonally around the body, accentuating Hathaway’s curves before pooling at her feet.

Anne Hathaway
Anne Hathaway at the 81st Academy Awards. (Credit: Image: Getty)

Angelina Jolie (2012)

Angelina Jolie showcased her sumptuous velvet Atelier Versace dress by playfully thrusting her leg out of the thigh-high split. The pose went viral and launched a thousand memes. Along with then-husband, Best Actor nominee Brad Pitt, the power couple dominated the media and Jolie’s pose became part of popular culture.

Angelina Jolie
ctress Angelina Jolie arrives at the 84th Annual Academy Awards. (Credit: Image: Getty)

Jane Fonda (2018)

The Oscars capped off an awards season that saw women band together and speak up against sexual harassment and abuse in the entertainment business. Led by the godmother of Hollywood protests, Jane Fonda, many sported a Time’s Up pin to show support.

Jane Fonda
Actor Jane Fonda attends the 90th Annual Academy Awards. (Credit: Image: Getty)

Billy Porter (2019)

A chance meeting with Christian Siriano inspired Billy Porter to take a stand in a tuxedo gown that embraced the gender fluidity dominating the social agenda. The velvet jacket, white shirt and black bow tie typical of a traditional gentleman were seamlessly combined with a classically feminine silhouette. It was “a walking piece of political art” that sought tolerance and said, “I am not a drag queen, I’m a man in a dress.”

Billy Porter
Billy Porter attends the 2019 Vanity Fair Oscar Party following the 91st Academy Awards. (Credit: Image: Getty)

Kristen Stewart, Timothee Chalamet and Zendaya (2022)

Young Hollywood’s biggest stars took the reins to redefining the red carpet in a way not seen since the late 1960s youth movement, and skin was definitely in. Dressed in Valentino, Zendaya’s cropped silk collared shirt had many recalling Sharon Stone’s 1998 look. Another star not bound by red-carpet rules, Kristen Stewart mixed rebellion with the elegance of Chanel, styling her haute shorts suit with an open shirt. Timothee Chalamet showed himself to be Hollywood’s leading male fashion icon, bucking gender- specific clothing in a sequinned black Louis Vuitton jacket with lace trim plucked from the spring 2022 womenswear runway.

Zendaya attends the 94th Annual Academy Awards. (Credit: Image: Getty)
Kristen Stewart turned heads on the 2022 Oscars red carpet. (Credit: Image: Getty)
Timothée Chalamet rocked a plunging neckline. (Credit: Image: Getty)

This is an edited extract from Red Carpet Oscars by Dijanna Mulhearn (Thames & Hudson, $100). Available now.

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