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Vintage Hollywood Legends Posing with Their Oscars

Winning an Oscar is one of the biggest achievements in Hollywood. These photos show vintage celebrities posing with their awards. Each picture captures a moment of pride and joy for these actors and filmmakers.

The Oscars were different back then compared to today. The ceremonies felt simpler, with fewer glitzy details. Yet the excitement was just as real. You can see it in the expressions on their faces. They hold their statues with a mix of happiness and disbelief.

Some winners wore formal outfits that reflect the fashion of their time. Men often chose classic tuxedos, while women wore elegant gowns. Their styles might look old-fashioned now, but they were perfect for their era. These outfits added to the special feel of the event.

The size of the audience was smaller in those days. Celebrities didn’t have to compete against as many people or movies. Still, winning meant just as much. It showed they stood out in their field. Holding that statue proved their hard work paid off.

Each photo tells its own story. Some winners smile brightly, showing how thrilled they are. Others look more serious, as if they’re still processing what happened. These moments remind us that even famous people feel nervous or surprised sometimes. Their reactions make them relatable despite their success.

#1 Vivien Leigh places the Oscar she won for her role as Scarlett in Gone With The Wind on her mantlepiece at home, 1940.

#2 Luise Rainer, the first woman to win two Oscars, holds her Best Actress award for her performance in The Great Ziegfeld during the 1937 Academy Awards ceremony.

#3 Joan Fontaine doing the household bookkeeping next to the Oscar she won for her role in Hitchcok’s Suspicion, 1942.

#4 Elizabeth Taylor at a Hollywood party with the Oscar she won for her role in Butterfield, 1961.

#5 Grace Kelly with the Oscar she won for her role in The Country Girl, 1955. William Holden, her co-star in the movie, stands behind her.

#6 Audrey Hepburn with the Oscar she won for Roman Holiday, 1954.

#7 Joanne Woodward smiles radiantly while holding her Best Actress Oscar for her role in Three Faces of Eve, 1958.

#8 Best Supporting Actor and Supporting Actress winners Frank Sinatra and Donna Reed (both for From Here to Eternity) and their Oscars, 1954.

#9 Bing Crosby (Going My Way), Ingrid Bergman (Gaslight) and Barry Fitzgerald (Going My Way) with their Oscars, 1945.

#10 Gloria Grahame with her Best Supporting Actress Oscar for The Bad and the Beautiful, 1953.

#11 Marlon Brando (right) with his Oscar for On the Waterfront, 1955.

#12 Onstage presenters seen from the wings during the 1950 Academy Awards.

#13 Jimmy Stewart, back from WWII, talks with the oldest employee of his family’s hardware store in Pennsylvania, George Little; nearby is a table of various mementos, including Stewart’s Best Actor Oscar for The Philadelphia Story.

#14 Joan Crawford with her Best Actress Oscar for Mildred Pierce, 1946.

Written by Rachel Mitchell

Rachel Mitchell is a vintage fashion enthusiast with a passion for all things retro. She is interested vintage fashion styles, trends, and accessories, and provides tips and tricks for incorporating vintage pieces into modern wardrobes.

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