He slept with Cary Grant and designed for Marilyn Monroe: new doc on outrageous Orry-Kelly

Acclaimed filmmaker Gillian Armstrong directs Women He's Undressed, about her famed fellow Aussie

Actor Darren Gilshenan plays designer Orry-Kelly in the documentary "Women He's Undressed." Image courtesy Wolfe Video

Renowned costume designer Orry-Kelly has been gone for over 50 years, but his legend lives on in Hollywood.

That is a testament in part to his extraordinary talent: he designed exquisite attire for some of the motion picture industry's greatest stars, including Bette Davis, Marilyn Monroe, Betty Grable, Natalie Wood and more. Ingrid Bergman's timelessly chic outfits in Casablanca? Those were his.

But stars like Jane Fonda, who was dressed by Orry-Kelly early in her career, also remember him for his vivid personality. He was "out" long before that was acceptable in Hollywood. 

Orry-Kelly's entertaining story is told in the documentary Women He's Undressed by acclaimed filmmaker Gillian Armstrong [My Brilliant Career, Little Women, Mrs. Soffel, Oscar and Lucinda]. The film is now playing at the Arena Cinema in Hollywood and becomes available on DVD in North America Aug. 9.

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Women He's Undressed from Wolfe Video on Vimeo.

Actors portray the young Orry-Kelly, the adult O-K, his mother and other key figures in his life, including a young Archie Leach [later to be known as Cary Grant]. The film suggests OK and Leach became lovers in New York [after Leach had emigrated from England and O-K had emigrated from Australia]. They remained on intimate terms in Hollywood until Leach/Grant became involved with Randolph Scott and then seemingly turned his back on his gay past by marrying a succession of women.

Armstrong's approach is altogether whimsical and airy, in keeping with the man she brings back to life. O-K had his ups and downs in Hollywood, drank to excess, but evidently never failed to be entertaining. There aren't really recreations in the film so much as imaginings of attitudes he may have taken and things he might have said. But there is no shortage of biography either, supplied in part by fellow costume designers and Hollywood historians.

Orry-Kelly puts finishing touches on an outfit for Marilyn Monroe. Photo courtesy Wolfe Video

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Orry-Kelly costuming actress Veda Ann Born, circa 1937. Photo courtesy Wolfe Video

There are wonderful anecdotes and remembrances from his colleagues and from Jane Fonda, who not only wore some of designs on film but socialized with him.

The gowns are on brilliant display and the film reveals many of the stories behind them -- how O-K managed to make Natalie Wood look more bosomy in Gypsy and how he practically flung Marilyn Monroe's shapely breasts at audiences in Some Like It Hot.

[Top] Natalie Wood in Gypsy; [right] Marilyn Monroe in Some Like It Hot. Via smh.com.au 

O-K also designed the women's gowns worn by Tony Curtis and Jack Lemmon in Some Like It Hot, which helped the actors deliver something crucial to the story -- a degree of plausibility that they could be mistaken for women.

​Orry-Kelly also was a gifted artist, as seems evident from the glimpses of his work that we see in the film. But once in Hollywood he gave his all to costume design, mostly at Warner Bros., at a time when the studio system was in full force and hundreds of pictures were built around female stars. His output was staggering.

Orry-Kelly's painting of a woman from the 1910s. Photo by Barbara Warner/courtesy Wolfe Video

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Nonfictionfilm.com will be speaking by phone with Armstrong from Australia next week. Look for our interview with her soon!

Orry-Kelly's costumes from Casablanca. Courtesy Warner Bros.

A movie still featuring costume work by Orry-Kelly. Courtesy Wolfe Video