Emil Jannings with his Best Actor Award at the 1st Annual Academy Awards, 1929.
Janet Gaynor receives the Best Actress Award at the 1st Annual Academy Awards Oscars (May 16, 1929 at the Hollywood Roosevelt Hotel)
Conrad Nagel presenting 1929 -1930 Best Actress Oscar to Norma Shearer for "The Divorcee" at The 3rd Annual Academy Awards Oscars (November 5, 1930). She wears a metallic brocade 2-piece dress adorned with mink cuffs and orchids trailing from her belt.
Shirley Temple presents the Best Actress Oscar to Claudette Colbert in 1936
Luise Rainer, in 1938. Even though German-born Rainer was nominated for Best Actress for her work in "The Good Earth", she stayed home the night of the ceremony in 1938—because she’d won the Best Actress statue the year before (for "The Great Ziegfeld"), and she figured there was no way she’d win two years in a row. But when word got out during the ceremony that indeed she was going to win again (the names of winners were released to the press), studio honcho Louis B. Mayer sent someone to pick up Rainer and quickly bring her to the ceremony. With no time to even apply makeup, Rainer accepted her award in her nightgown—which was high-necked, long-sleeved, and, fortunately, gorgeous. "It was the nicest dress I owned," said Rainer.
1939: Spencer Tracy and Bette Davis attend the Academy Awards dinner. Bette Davis holds her Best Actress award for "Jezebel".
Vivian Leigh at an after-party at the Coconut Grove in 1940, holding her Oscar for "Gone With The Wind". According to contemporary sources, the featherweight dress was a chiffon silk printed with bold red poppies on green stems.
At the 1942 Academy Awards, Joan Fontaine gazes at the Best Actress Oscar she won for her role in "Suspicion" — an achievement that made her, incredibly, the only actor or actress to ever win an Oscar for a performance in an Alfred Hitchcock film.
Actress Jennifer Jones holds her Academy Award won for Best Actress for her role in the 1943 drama "The Song of Bernadette" during the 16th Academy Awards
Elizabeth Taylor at age 17, presenting the 1949 Academy Award for Best Costume, dressed in an antebellum-style tiered gown
Marilyn Monroe holding, not an Oscar, but the Henrietta Award she received for "The Best Young Box Office Personality" in 1952
Tony Curtis and Janet Leigh, Hollywood’s golden couple at the time, attending the 1953 Academy Awards - the first televised Oscars.
John Wayne holds Oscars for Gary Cooper and John Ford for Best Actor and Director, respectively, for High Noon, backstage at the 25th Academy Awards at the RKO Pantages Theatre, Hollywood, 1953.
Not Oscar-related but I wanted to include this. Marilyn Monroe and Betty Grable attend Walter Winchell's birthday party at Ciro's Restaurant in 1953
1953: “He was so proud of me that night,” says Terry Moore (a supporting actress nominee for "Come Back, Little Sheba") of her date, Roger Wagner, who lifted a chain in front of the theater so that Moore could go in — the couple had missed the entrance for the red carpet.
Audrey Hepburn accepted her 1954 Best Actress statue (for "Roman Holiday") wearing a delicate floral-patterned belted dress by Hubert de Givenchy featuring the boat-neck style Hepburn favored. Hepburn was Givenchy's muse—and this dress was a perfect example of the designer's ability to craft clothes that reflected the gamine actress's unique blend of sophistication and sweetness.
Producer Buddy Adler's Academy Award for "From Here to Eternity" stands amid hats in the coat check room at Romanoff's restaurant in Beverly Hills during an Oscars after-party in 1954
1954: Esther Williams tells Donna Reed that she had her fingers crossed for her outside the ladies room at the Romanoff's after-party, the night Reed won Best Supporting Actress for her performance in "From Here to Eternity."
Eight-time Oscar winner (and 35-time nominee), Edith Head, who designed costumes for Hepburn and Hedren among others, shown here after her 6th Oscar for the movie "Sabrina".