Never having heard the name Orry-Kelly isn’t much of a surprise for individuals not distinctly interested in Old Hollywood or in costume design, but as Women He’s Undressed reveals, he was damn near everywhere in film from the 30s to the 60s. Not only was the man the winner of three Academy Awards (for An American in Paris, Les Girls, and Some Like It Hot), he also dressed actresses like Bette Davis (Now, Voyager), Ingrid Bergman (Casablanca), and Rosalind Russell (Auntie Mame), gave Humphrey Bogart his iconic Maltese Falcon look, and helped Busby Berkeley give his wildly visual films and set pieces (42nd Street, Gold Diggers of 1933) the perfect gowns to go with them.

Gillian Armstrong’s documentary dives right into the life and career of Australian costume designer Orry-Kelly by blending archival footage, talking head interviews, and having an actor (Darren Gilshenan) perform as him by delivering segments from his tell-all memoir Women I’ve Undressed. While the first two are standard documentary fare, Armstrong has a blast with the third, allowing Gilshenan to campily deliver every bit of dialogue he’s given. Almost as sporadic as a Baz Luhrmann film (whose regular collaborator and exquisite costume designer Catherine Martin appears here), she cuts between Orry-Kelly in a rowboat monologuing about his life, an actress who plays his mother musing on what he’s up to, and simply-decorated backlots lit like a Sirk film in which Gilshenan cavorts with a number of models (all of which are stand-ins for real people) and dishes the good Old Hollywood gossip.

And gossip is exactly what makes up a good chunk of Women He’s Undressed, particularly every ounce of Orry-Kelly’s life that was tangibly associated with Cary Grant and his rumored homosexuality. As somewhat overused as the discussion of Grant’s sexuality is in the film, it’s unsurprising that this material is included, as homosexuality was distinctly tied to Orry-Kelly’s career traction and alcoholism. While some interviewees feign unawareness at why his alcoholism came about, costume designer Ann Roth at one point quite bluntly states that being gay and working within a studio system in the 40s was enough to make anyone an alcoholic. But the film offers a number of interesting stories about the costume designer working with famous actresses, particularly his time with Bette Davis, in which the two often seemed locked in battle against Jack Warner to get what they wanted (and what ultimately looked better and more authentic on screen).

Having a number of costume designers—Kym Barret, Michael Wilkinson, Colleen Atwood and the aforementioned Martin and Roth, among many other individuals—discussing Orry-Kelly’s gowns alongside their images works wonderfully, even though the film’s editing doesn’t always jive as well as it should. It may seem as though Women He’s Undressed doesn’t try to be anything other than somewhat educational pop-filmmaking fluff about an oft-forgotten figure in Old Hollywood, but Armstrong lends what could have been a disembodied voice for Orry-Kelly some genuine humanity in the way she presents him. She’s made a fitting film for a man who loved dressing women as much as he loved gossiping with them; one that leaves the viewer wanting to (re)visit a bunch of classics and high-five Jane Fonda after she talks about wanting to motorboat Marilyn Monroe in her Some Like It Hot dress. 

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Directed by Gillian Armstrong; written by Katherine Thomson; starring Darren Gilshenan, Deborah Kennedy, and Louis Alexander; 95 minutes.

Women He’s Undressed will be playing in Miami during the MiFo LGBT Film Festival on Sunday, May 1st, at 5:00 p.m. at the Miami Beach Cinematheque.