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Audrey Hepburn holding the Academy Award for Best Actress © Bettmann

Vintage Oscars photos: Audrey Hepburn, Elizabeth Taylor, Sylvester Stallone and more stars

From Audrey Hepburn’s stunning Givenchy gown to the elegance of Grace Kelly.


Daniel Neira
Daniel Neira - Los Angeles
Senior WriterLos Angeles
FEBRUARY 28, 2025 8:33 PM EST

The Academy Awards have long been a symbol of Hollywood’s glamour and elegance, celebrating iconic and impactful movies. Now that we are preparing for the upcoming ceremony, we take a look back at some of the best moments of the Oscars, including Rita Moreno's win for 'West Side Story' and Dustin Huffman and Meryl Streep's sweet celebratory moment.

Take a peek at some of the best vintage photos from the Academy Awards, showcasing fashion moments involving some of the most fan-favorite celebrities and A-list stars. From Audrey Hepburn’s stunning Givenchy gown to the elegance of Grace Kelly, and the timeless beauty of Elizabeth Taylor. 

The Oscars may evolve year after year, but these iconic images remind us that the magic of the event lies not just in the awards, but in the timeless charm of the stars, the films, and the undeniable allure of Hollywood.

Jean Simmons and Cary Grant (1958)© Bruce Bailey

Jean Simmons and Cary Grant (1958)

Jean Simmons with the Oscar she accepted on behalf of Alec Guinness, for his role in 'The Bridge on the River Kwai', with presenter Cary Grant, at the 30th Academy Awards.

Marlon Brando, Bette Davis and Grace Kelly (1955)© Screen Archives

Marlon Brando, Bette Davis and Grace Kelly (1955)

Marlon Brando and Grace Kelly hold their Oscar statuettes following their win for 'On the Waterfront' and 'The Country Girl', respectively, at the 27th  Academy Awards, with presenter Bette Davis standing beside them.

Barbara Streisand (1969)© Bettmann

Barbara Streisand (1969)

Barbara Streisand poses with her Oscar after receiving a special recognition for her role in 'Funny Girl.'

Academy Award winner Cher backstage with her Oscar award, April 11,1988 in Los Angeles, California.© Bob Riha Jr

Cher (1988)

Academy Award winner Cher is all smiles backstage posing with her Oscar award.

Sylvester Stallone (1977)© Michael Ochs Archives

Sylvester Stallone (1977)

Sylvester Stallone was photographed during the 49th Academy Awards, nominated for two awards 'Best Original Screenplay' and 'Best Actor', both for 'Rocky.'

Audrey Hepburn (1954)© Hulton Archive

Audrey Hepburn (1954)

Audrey Hepburn is surrounded by reporters as she holds the Best Actress Oscar she won for her role in director William Wyler's film, 'Roman Holiday,' at the Academy Awards ceremony.

Rita Moreno (1962)© Bettmann

Rita Moreno (1962)

Rita Moreno was photographed smiling after winning in the Best Supporting Actress category for her iconic performance as Anita in the musical film West Side Story.

Jane Fonda (1979)© Paul Harris

Jane Fonda (1979)

Jane Fonda wins in the Best Actress category for the film 'Coming Home' at the 51st Academy Awards ceremony.

Elizabeth Taylor (1967)© Keystone

Elizabeth Taylor (1967)

Elizabeth Taylor is photographed holding the Oscar she won for the film 'Who's afraid of Virginia Woolf.'

Paul Newman and Joanne Woodward (1958)© Darlene Hammond

Paul Newman and Joanne Woodward (1958)

Joanne Woodward holds her Oscar statuette while sitting next to her husband, Paul Newman, during the Governor's Ball, an Academy Awards party held at The Beverly Hilton Hotel.

Grace Kelly (1954)© Bettmann

Grace Kelly (1954)

A smiling Grace Kelly holds her Oscar after winning the coveted Academy Award for Best Actress following her role in 'The Country Girl.'

Dustin Hoffman and Meryl Streep (1980)© Bettmann

Dustin Hoffman and Meryl Streep (1980)

Dustin Hoffman and actress Meryl Streep smile happily after winning their respective Oscars. Hoffman won his Oscar for the Best Actor Award for his role in 'Kramer vs. Kramer' and Streep won her Oscar for Best Actress In a Supporting Role for her role in the same film.

Gloria Estefan (1988)© Vinnie Zuffante

Gloria Estefan (1988)

Cuban-American singer Gloria Estefan and her romantic partner, Cuban-American musician and producer Emilio Estefan, attend the 60th Annual Academy Awards.

Lionel Richie (1986)© Bettmann

Lionel Richie (1986)

Lionel Richie kisses his Oscar after winning the award for Best Original Song with 'Say You, Say Me' from 'White Nights.'

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