21 Vintage Oscars Photos That Showcase the Glamour of Old Hollywood

21 Vintage Oscars Photos That Showcase the Glamour of Old Hollywood

Hollywood is virtually synonymous with glitz and glamour, and nothing showcases that more than the Academy Awards. Since 1929, celebrities and Tinseltown luminaries have celebrated the year’s best films and performances. Also referred to as simply the Oscars (the name was officially adopted in 1934), the star-studded ceremony has captivated audiences since its debut broadcast and has continued to be a mainstay in pop culture for nearly a century.

Want to take a glamorous trip back in time? We’ve compiled a collection of vintage Oscar photos that put a spotlight on the elegance of Old Hollywood. From dapper suits to flapper-style ensembles, these retro photos depict moments in history where conservative and classy looks were center stage. Whether it’s Mary Pickford’s scene-stealing finger waves, Grace Kelly’s chartreuse satin gown or Hattie McDaniel’s cascading corsage, these flashbacks are undeniably timeless.


1929

The Academy of Motion Picture Arts and Sciences hosted its first awards ceremony on May 16, 1929 in a banquet hall at the Hollywood Roosevelt Hotel.

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There were 270 guests in attendance. The price to be amongst the leading stars of the time? Only $5, which would be approximately $93 today.

In this photo, William C. Demille, President of The Academy (left) hands the Oscar for Best Actress to Mary Pickford for her role in My Best Girl and bestows the award for Best Actor to Warner Baxter (right) for his role in Old Arizona.

vintage oscars photos, mary pickford, warner baxter and hans kraly receiving an oscar 1929
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1930

Canadian star Norma Shearer receives a Best Actress Oscar from Conrad Nagel for her role in The Divorce. The two co-starred as love interests in the film, which was directed by Robert Leonard.

Shearer's finger waves hairstyle was a popular look for women throughout the 1920s and early 1930s

vintage oscars photos, best actress
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1932

Actress Helen Hayes took home the Best Actress award for her portrayal of Madelon Claudet in The Sin of Madelon at the 5th Annual Academy Awards held at the Ambassador Hotel in Los Angeles, California, on November 18, 1932.

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Her pearl necklace and V-neck style dress displayed a sophisticated look that many women of the era gravitated towards for upscale events.

vintage oscars photos, 5th annual academy awards
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1935

Clark Gable holds his Best Actor Oscar for his role in It Happened One Night... He was awarded the golden statuette and had a formal dinner held at the Biltmore Bowl in Los Angeles, California, on February 27, 1935.

His tailored dark suit topped with a striking white bow tie is a classic look that is often replicated today

vintage oscars photos, clark gable with oscar statuette
Bettmann - Getty Images


1938

Hollywood legends Spencer Tracy and Bette Davis are shown holding their Oscars at the Academy Awards ceremony. Davis won for her role in Jezebel, while Tracy took it home for his performance in Boys Town.

vintage oscars photos, spencer tracy and bette davis...
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1940

Actress Fay Bainter (right) presents Hattie McDaniel (left) the Academy Award for her supporting role in Gone With the Wind, at the 12th annual Oscars.

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McDaniel was the first African American woman to receive an Academy Award.

The trailblazing actress and singer-songwriter dons an eye-catching floral hair accessory that's accentuated by a cascading corsage that rounds out her memorable ensemble.

vintage oscars photos, hattie mcdaniel, left, gets academy award
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1941

American actors James Stewart and Ginger Rogers look lovingly into each others eyes while their arms are interlocked at the Oscars held on February 27, 1941.

Stewart won Best Actor in a Leading Role for his performance in The Philadelphia Story while Rogers won Best Actress in a Leading Role for her performance in Kitty Foyle: The Natural History of a Woman.

vintage oscars photos, stewart and rogers celebrate oscar wins
Hulton Archive - Getty Images


1945

Ingrid Bergman in 1945 with the Oscar she received for her performance in Gaslight, in which she co-starred with Charles Boyer.

Bergman's face-framing curls were all the rage for many women during the 1940s. The style was typically achieved by using rollers, pins, and setting lotion.

vintage oscars photos, ingrid bergman holding oscar award
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1949

Actor Douglas Fairbanks accepted the Oscar on behalf of his friend Sir Laurence Olivier for his role in Hamlet, from Loretta Young, at the 21st Academy Awards in Los Angeles on March 24, 1949.

vintage oscars photos, douglas fairbanks jnr and loretta young
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1953

Gloria Grahame gives her best-supporting actress Oscar a smooch at the 25th Annual Academy Awards. She won the coveted statuette for her performance in The Bad and the Beautiful.

vintage oscars photos, gloria grahame receives oscar award
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1954

Legendary actress Audrey Hepburn with her award for Best Actress for her role in the film Roman Holiday at the 26th Academy Awards at the NBC Century Theatre in New York City. She's standing in between actor Fredric March (left) and Danish-American actor Jean Hersholt, the former President of the Academy, on March 25, 1954.

Hepburn, known for her polished style, is wearing a dress designed by Givenchy.

vintage oscars photos, audrey at the oscars
Archive Photos - Getty Images


1954

Actress Donna Reed poses with her Academy Award for Best Supporting Actress in From Here to Eternity in Los Angeles, California.

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Her sweetheart neckline frock is a standout that boasts a flattering and timeless silhouette.

vintage oscars photos, donna reed
Michael Ochs Archives - Getty Images


1955

Edmond O'Brien and Grace Kelly with their Oscars at the 27th annual Academy Awards ceremony, held at the RKO Pantages Theatre in Hollywood on March 30, 1955.

O'Brien won Best Supporting Actor for his performance in The Barefoot Contessa, and Kelly won Best Actress for her performance in The Country Girl.

Grace is wearing a seafoam green satin gown with double spaghetti straps complemented by a ruched skirt. The dress was designed by Edith Head, a prolific costume designer who worked in the industry from the 1930s through the 1970s.

vintage oscars photos, kelly and o'brien at the oscars
Silver Screen Collection - Getty Images


1956

Actors Cleo Moore (left) and Jayne Mansfield (right) strike a hot pose in front of a life-size Oscar statue at the Academy Awards on March 25, 1956.

vintage oscars photos, pout and leer
Hulton Archive - Getty Images


1957

Actors Robert Wagner and Natalie Wood seated at an Academy Awards party at the Beverly Hilton.

Wood's ornate bow-emblazoned neckline is a striking detail that adds charm to her sweet ensemble.

vintage oscars photos, wagner and wood
Darlene Hammond - Getty Images


1957

Robert Stack and his wife actress Rosemarie Bowe flaunt their beautiful smiles at the 29th annual Oscars ceremony.

Bowe's strapless dress accentuates her décolletage while Stack's elongated lapels add a sharp detail.

vintage oscars photos, academy awards
Michael Ochs Archives - Getty Images


1958

Actress Joanne Woodward, wearing a strapless ball gown with white evening gloves at the 30th Academy Awards press room, at the RKO Pantages Theatre in the Hollywood on March 26, 1958.

Woodard was the first person to win an Oscar for portraying three different personalities in the film The Three Faces of Eve.

vintage oscars photos, academy awards
Michael Ochs Archives - Getty Images


1961

Elizabeth Taylor at the 33rd annual Academy Awards on April 17, 1961.

The iconic actress' bouffant hairdo was a popular style in the late 1950s and early 1960s. She's wearing a gown designed by Marc Bohan for Christian Dior, accessorized with long evening gloves. Her glamorous look is punctuated by diamond and pearl droplet earrings.

vintage oscars photos, elizabeth taylor with oscar
Archive Photos - Getty Images


1961

Actress Shirley Temple Black wears a blue and silver dress as she presents Annette Funicello the Juvenile Academy Award on behalf of Hayley Mills at the 1961 Academy Awards.

vintage oscars photos, academy awards
Bettmann - Getty Images


1963

Actors Gregory Peck, Sophia Loren, Joan Crawford, and Maximilian Schell stand backstage at the 35th Academy Awards at the Santa Monica Civic Auditorium in Los Angeles, California.

Peck is holding his Oscar for Best Actor for his role in the iconic film To Kill a Mockingbird, while Crawford holds the trophy she accepted on behalf of Anne Bancroft for her Best Actress win for her portrayal in the film The Miracle Worker.

vintage oscars photos, backstage at 1963 oscars
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1964

Actor Sidney Poitier is holding his Academy Award for Best Actor in a Leading Role for Lilies Of The Field, directed by Ralph Nelson, at the 36th Academy Awards ceremony.

Poitier became the first Black actor to win in this category.

vintage oscars photos, sidney poitier receiving oscar
Bettmann - Getty Images

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