Ask a random sampling of movie buffs to name a famous costume designer and the first response will most likely be Edith Head, and rightfully so. With 35 Oscar nominations to her name (eight of which went on to win), Head is synonymous with high-calibre movie fashion. Ask for additional names, and the hardcore film fans will reveal themselves, offering names like Irene Sharaff, Charles LeMaire, and Milena Canonero. Another designer they might mention is Orry-Kelly, son of Australia, winner of Academy Awards, and a man whose story is as fascinating as they come. That story is told to remarkable effect by filmmaker Gillian Armstrong in her documentary, Women He’s Undressed.

The linear bio starts with the boyhood days of Orry George Kelly, the son of a tailor from Kiama, New South Wales, Australia. Those early days reveal two key things that will forever shape Kelly’s career and life: his natural and immense artistic flare, and his homosexuality. Living in a land during a time when the latter was not tolerated, Kelly abandons the banking career he had begun and departs Australia in 1922 to set sail for America. In his early years in New York City, Kelly makes his bones as an artist and costumer for Broadway productions. It’s also during this time he begins a romantic relationship with Archie Leach, a struggling (but unspeakably handsome) actor who eventually goes on to change his name to Cary Grant.

The two make it to Hollywood together, but where their individual careers began to thrive, their relationship died. Cary Grant goes on to be, well, Cary Grant, while Orry-Kelly goes on to costume some of Hollywood’s greatest stars (Bette Davis-calibre) in over 280 films (including a little picture called Casablanca), winning three Oscars in the process.

There is some deft storytelling from Gillian Armstrong in Women He’s Undressed. This isn’t just another biopic about a kid from the middle of nowhere making it big in showbiz, nor is it just some revelation about another unsung Hollywood behind-the-scenes great, nor is it just a name-dropping clip reel of Hollywood history. It’s actually all of these things and more. And it’s dazzling.

Women He’s Undressed might struggle to get out of the gate of his childhood, but during those early minutes of the film, his homosexuality is established. This is key not only because it makes him who he is, but because the position and evolution of the entertainment industry (somewhat Broadway, mostly Hollywood) as it relates to same-sex relationships has considerable consequences. The greater narrative then radiates from Orry-Kelly: he’s gay, others in Hollywood are gay, here is how Hollywood handled gay. (The approach towards his sexual orientation, by the way, is never disrespectful, nor does it ever pander.)

Bringing Archie Leach/Cary Grant into the story might sound scandalous (and it is), but it is also critical to the designer’s tale in that: (a) Leach/Grant is a major love of Orry-Kelly’s life, and (b) the actor is responsible for Orry-Kelly making it to Hollywood. This isn’t just a kiss-and-tell; Leach/Grant has real purpose to who Orry-Kelly is as a person and as a costume designer.

Once the story moves inside Hollywood’s gates, Armstrong really shows what she’s made of as a documentarian.

The Orry-Kelly thread about his homosexuality turns into the fabric of a Hollywood history lesson. Like the same-sex narrative, the Hollywood history narrative radiates from Orry-Kelly, puts context around the time and the business, then returns to put Orry-Kelly into history’s context and vice versa.

The history radiates to the groundbreaking work that Busby Berkley did and then brings it back to Orry-Kelly’s equally impressive costumes for the filmmaker’s pictures. The history radiates to the tawdriness of pre-code films and crosses over to the more subdued post-code films, using Orry-Kelly as a bridge between the two eras and focusing on what he did as a costumer during both eras (including what he got away with, post-code). Then to some of the titans of the times: Bette Davis, Jack Warner, William Randolph Hearst, Marilyn Monroe—and his relationships with all of them. And of course, the story then proceeds to Cary Grant. The documentary even finds its way back to Australia from time to time.

By the time the story is over, Orry-Kelly is not just another Hollywood luminary—he’s forever one with that town and its history.

Yet for all its narrative might, some of the storytelling devices employed fall terribly flat. Armstrong opts to cast people to play Orry-Kelly and his mother, and then work them into the story for narration, commentary, even humor. It’s all so silly, especially in the earliest days, which at times are downright cartoonish. I think I get what Armstrong is trying do—inject elements of stage and film into these portions as representations of the two branches of entertainment where Orry-Kelly was at his best. It just feels so gimmicky, and never more so than when the intricate pattern Armstrong weaves suddenly gets disrupted. Also feeling manufactured are quotes from celebrities as voiced by other actors. It’s intrusive and too cute by half, and it’s all to the detriment of the overall product.

It wouldn’t be a documentary without some talking heads, and it’s refreshing to see some living legends who worked with Orry-Kelly offer their thoughts. The most recognizable are critic/historian Leonard Maltin, actress Angela Lansbury, and actress Jane Fonda. (Hearing Fonda confess to what she would have liked to have done to a certain part of Marilyn Monroe’s anatomy is worth the price of admission.) These celebs, and other contributors, are used in excellent measure. Oddly enough, Orry-Kelly himself is only ever seen (via photos) at the end of the film.

Orry-Kelly’s formidable combination of history, skill, attitude, and pizzaz creates a mighty base for Armstrong to build upon, and build she does, using numerous storytelling devices and a whip-smart narrative. Women He’s Undressed isn’t always perfect, but it’s riveting from start to finish.