Orry-Kelly was born in Kiama, New South Wales, Australia, and was known as Jack Kelly. His father William Kelly was born on the Isle of Man and was a gentleman tailor in Kiama. Orry was a name of an ancient King of the Isle of Man. Orry-Kelly was sent to Sydney at age 17 to study banking and there developed his love of theatre. Orry-Kelly journeyed to New York to pursue an acting career and shared an apartment there with Charles Phelps AKA Charlie Spangles and Cary Grant. A job painting murals in a nightclub led to his employment by Fox East Coast studios illustrating titles. He designed costumes and sets for Broadway’s Shubert Revues and George White’s Scandals. He served with the United States Army Air Corps during World War II until being discharged for alcohol problems. After moving to Hollywood in 1932, Orry-Kelly was hired by Warner Bros. as their chief costume designer and he remained there until 1944. Later, his designs were also seen in films at Universal, RKO, 20th Century Fox, and MGM studios. He won three Academy Awards for Best Costume Design (for An American in Paris, Cole Porter’s Les Girls, and Some Like It Hot) and was nominated for a fourth (for Gypsy). Orry-Kelly worked on many films now considered classics, including 42nd Street, The Maltese Falcon, Casablanca, Arsenic and Old Lace, Harvey, Oklahoma!, Auntie Mame, and Some Like It Hot. He designed for all the great actresses of the day, including Bette Davis, Kay Francis, Olivia de Havilland, Katharine Hepburn, Dolores del Río, Ava Gardner, Ann Sheridan, Barbara Stanwyck, and Merle Oberon. Orry-Kelly was known for his ability to “design for distraction” to compensate for difficult figure shapes. He also had the job of creating clothes for the cross-dressing characters played by Tony Curtis and Jack Lemmon in Some Like It Hot. He wrote that when he finished draping Dolores del Río in white jersey, “she became a Greek goddess … she was incredibly beautiful”. The elegant clothes he designed for Bergman’s character in Casablanca have been described as “pitch perfect”.

In addition to designing, Kelly wrote a column, “Hollywood Fashion Parade”, for the International News Service, owned by William Randolph Hearst, during the years of World War II. Kelly’s memoirs, entitled Women I’ve Undressed were discovered in the care of a relative, as a result of publicity surrounding Gillian Armstrong’s 2015 documentary on Kelly, Women He’s Undressed. The memoir was published for the first time in 2015. A longtime alcoholic, Orry-Kelly died of liver cancer in Hollywood and was interred in the Forest Lawn Memorial Park, Hollywood Hills. His pallbearers included Cary Grant, Tony Curtis, Billy Wilder and George Cukor and his eulogy was read by Jack L. Warner. He had no living relatives when he died so his personal effects and Academy Awards were stored by Ann Warner, wife of his friend, Jack. The Oscars were among the items scheduled for exhibition entitled Orry-Kelly: Dressing Hollywood, in the Australian Centre for the Moving Image in August 2015.