The side cutout and floral print dress was way ahead of its time when Leigh wore it to the awards for her Oscar-winning performance as Scarlett O'Hara in 1939's "Gone With The Wind."
Hepburn attended the 1954 Academy Awards (straight after performing in Broadway's "Ondine," no less) in this lace Givenchy gown, where she won Best Actress for her portrayal of Princess Anne in 1953's "Roman Holiday."
Famed costume designer Edith Head created this icy blue gown that Kelly would accept the Best Actress Oscar in for her performance alongside Bing Crosby in 1954's "The Country Girl."
Loren presented David Lean with the Best Director award for "The Bridge On The River Kwai" in this classic cut floral print dress with diamond drop earrings and necklace. Loren would later win the first Oscar for a foreign language performance in 1961 for her performance in the Italian film "Two Women."