You know the films, you know the stunning gowns, but do you know who designed them? Even in his native Australia, the three-time Academy Award-winning designer of CASABLANCA, THE MALTESE FALCON, GYPSY, IRMA LA DOUCE among others is a complete unknown; even to filmmaker Gillian Armstrong (MY BRILLIANT CAREER) and award-winning costume designer Catherine Martin (MOULIN ROUGE) whose costumes for Baz Luhrman's spectacles were certainly inspired by the works of Orry-Kelly. Born in Kiama, New South Wales in 1897 into wealth and exposed to art and culture at an early age, Orry George Kelly (played in performance segments throughout the documentary by DARK CITY's Darren Gilshenan) nevertheless moved to Sydney as a teenager to study and become a banker as desired by his mother (dramatized by SWIMMING UPSTREAM's Deborah Kennedy) but found himself drawn to the seedier theater district and into a relationship with the city's most notorious pickpocket before fleeing to New York with a ticket bought by his mother (who assumed he had gotten a girl "in trouble"). He found freedom to be himself in the Greenwich Village of the twenties and his first great love in another penniless immigrant of similar background: the English Archibald Leach. Bachelor "roommates", Orry found work in nightclubs and the stage in set dressing and wardrobe while Archie worked as an escort to wealthy ladies. Both would make their separate ways to Hollywood, Archie by landing a screen test at Paramount, and Orry following speak easy owner Belle Livingstone to Reno and then to Los Angeles where Archie (now Cary Grant) got him work in the wardrobe department at Warner Bros. He soon became the designer of choice for actresses both opinionated about how they looked and as well as those of "difficult" figure shapes from Ruth Chatterton (THE RICH ARE ALWAYS WITH US), Kay Francis (WIFE WANTED), Barbara Stanwyck (BABY FACE), Dolores Del Rio (BIRD OF PARADISE), and Bette Davis - an actress whose looks and figure were the subject of some of Hollywood's most vicious criticism but who was unafraid to look unflattering for the sake of a role - in films like JEZEBEL (a monochrome film in which Davis made a splash by showing up at a black and white ball in red), NOW, VOYAGER, DARK VICTORY, THE LETTER, MR. SKEFFINGTON, and THE PRIVATE LIVES OF ELIZABETH AND ESSEX where Orry-Kelly (as he had been rechristened to sound "Parisienne") and Davis battled director Michael Curtiz for authenticity. Drafted at age forty-six, Orry-Kelly found himself no longer in demand and looking for work at other studios (he considered dressing Betty Grable a nightmare). He also got to indulge his extravagant design sense in musicals, particularly the visionary works of Busby Berkeley starting with 42ND STREET.

In the aftermath of his long stay at rehab, Orry-Kelly earned a reputation as being difficult and foul-mouthed; and yet, it was during this period that he achieved his greatest notice with three Academy Awards (the award for costume design having been added in 1948) with wins for AN AMERICAN IN PARIS - shared with Walter Plunkett (GONE WITH THE WIND) and Irene Sharaff (WEST SIDE STORY) - LES GIRLS, and SOME LIKE IT HOT. In the ensuing years, the credits were not always so lofty, but Orry-Kelly became the favorite for a new generation of actresses including Natalie Wood, Jane Fonda, and Rosalind Russell before his untimely death at age 66 while working on KISS ME STUPID. The film explores Orry-Kelly's life through his memoirs, the biographies and autobiographies of those he worked with, the letters he wrote to his mother (which formed the basis of his memoirs), and the memories of those still alive who knew him from Angela Lansbury (THE PRIVATE AFFAIRS OF BEL AMI) - who felt herself a "character actress" rather than a glamorous star - Fonda, Barbara Warner Howard (daughter of Jack Warner), and producer Eric Sherman (son of director Vincent Sherman who worked with Orry on films like OLD ACQUAINTANCE) to costume designer Ann Roth (DRESSED TO KILL and Jean Mathison (administrative assistant to Billy Haines who walked away from his contract as an actor rather than renounce his gay lifestyle and went on to become a famous interior designer) as well as Scotty Bowers, ex-marine/escort turned Hollywood "party service" pimp who knew Orry-Kelly intimately. The part of the documentary dealing with Orry-Kelly's sex life is not really an expose of his partners - although it does not cast Grant in a good light, having distanced himself from Orry and his subsequent "buddy" Randolph Scott (WESTERN UNION) for a series of marriages, the expiration dates of which were predicted as they were announced - and his friends as much as a portrait of what it was like to be gay during the golden age of Hollywood when such things were not talked about. The influence of Orry-Kelly's designs is discussed by costume designers Roth, Martin, and Colleen Atwood (MEMOIRS OF A GEISHA), Deborah Nadoolman (RAIDERS OF THE LOST ARK, Michael Wilkinson (AMERICAN HUSTLE), and Kym Barrett (THE MATRIX) as well as film historians Leonard Maltin, Marc Eliot, David Chierichetti, and costume collector Larry McQueen.