Felicity Chandelle (1905–2008), Pilot and Crossdresser

Felicity Chandelle (1905–2008), Pilot and Crossdresser

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By Jan Brown and Dallas Denny

This photo of Felicity Chandelle initially appeared in Mariette Pathy Allen’s book Transformations. Felicity is sitting in a chair in front of an old photograph of her mother and a child. That child is Felicity, dressed as a young girl.

Felicity Chandelle—known in some circles as Captain John MacDonald Miller—was present at the very beginnings of gatherings of crossdressers on the East Coast of the United States. She led a long and distinguished life in both of her modes of presentation. This article is based upon a workshop we did together about Felicity at TransWeek 2023. If TransWeek is a name unfamiliar to you, know that it was formerly called Fantasia Fair. This year marked the 49th annual gathering in Provincetown, on the very tip of Cape Cod. Next year, the 50th, will be a blow-out event, and you are invited. If you are reading this you are welcome, of course, to register, but if you just show up in P’Town you’ll find others like yourself with whom you can socialize, fine dining, free admission to daily keynotes, and tickets for sale at low prices to three of our evening events. Come if you can. The dates for TransWeek 2024 are October 20 through 27.

Our workshop came about because Jan and Felicity were friends. Before Felicity passed away at age 102, Jan helped her donate her crossdressing materials to the LGBT Center in New York City, where they’re available to view and study. Jan wound up with two photo albums from 1961 and 1962; we recently scanned the more than two hundred photos. The images will soon be added to the wonderful Digital Transgender Archive, but for now you can peruse them on Dallas’ Google Drive.

We begin with the story of Captain Johnny Miller.

Captain John MacDonald Miller


At age ten, in 1915, young John Miller was spending his free time at the Curtiss Flying School at Mineola, on Long Island. There, Zagria Cowell writes in her Gender Variance Who’s Who website, “she encountered Ruth Law, the third American woman to get a flying license.” By seventeen, Miller had taught himself to fly and was earning money by barnstorming and giving rides to pleasure-seeking customers. He was the stunt flyer for the 1935 film Ladies Crave Excitement.

In 1931, Miller was the first person in America to buy a PCA-2 autogyro, which could perform nearly vertical ascents and descents. He was the first to make a transcontinental flight across North America in a gyrocopter; for this, he was in competition with Amelia Earhart. Miller knew, among others, Amelia and Charles Lindbergh; he was present when Lindbergh took off from Roosevelt Field on Long Island for his successful nonstop flight across the Atlantic Ocean.

Captain Miller Takes Off from the Roof of the U.S. Post Office in Philadelphia, 1935.

Miller flew mail for the US Post Office and is known for the first mail delivery by gyrocopter. On May 27, 1935, he departed from the roof of the post office building in downtown Philadelphia and landed in Camden, New Jersey. He served as a pilot in the Marine Reserve and as a qualified naval aviator. In 1937, while serving as a test pilot for the Kellett Autogiro Company, his aircraft disintegrated around him, leaving him, according to various sources, either relatively unscathed or with a broken neck.

Miller was one of the earliest airline pilots. He began flying for United Airlines in 1936 and switched to Eastern Airlines in 1939. He was an airline pilot until 1964, when he was fired after public exposure following an arrest in New York City for having violated an anti-masking law by being crossdressed. He pled not guilty and was convicted, whereupon he took his case all the way to the U.S. Supreme Court, which refused to consider it.

One of Fourteen Paintings of Lee Miller by Pablo Picasso.

Four of Captain Miller’s aircraft are preserved in the Air and Space Museum in Washington, D.C. He was chosen as one of two pilots honored at the 100th anniversary of the Wright Brother’s first flight at Kitty Hawk; the other pilot was Neil Armstrong, the first person to set foot on the moon.

Captain Miller was married twice, both times to women who knew of his crossdressing. He and Katherine, his first wife, had three children. After her death in 1963, he married, Edith, a physician. She died in 1991.

John’s older sister Lee was a live-in companion of painter Pablo Picasso and the subject of fourteen of his paintings. Felicity said that when Johnny was young, Lee would dress him as a girl.

John Miller was an exceptional pilot and by all accounts an exceptional human being. There’s so much more we could say about him! Here’s just one tidbit: He held a patent for a rifle scope mount of his invention, the first that would stay in register after the scope was removed and reinstalled. He manufactured the mounts in his garage and sold them worldwide.

Miller, who spent his early days on Long Island, eventually moved to Poughkeepsie, where he met Jan.

John Miller died in 2008 at age 102 of natural causes, two years after his last flight, at age 100. He holds the record for being the world’s oldest pilot. His last words to his nephew were “I guess my flying days are over.”


Felicity Chandelle, 11-12-1961, Posing with a Friend’s Corvette.

Apart from a couple of childhood incidents, John didn’t crossdress until 1960, when she took up the practice with enthusiasm.

“There was absolutely no sexual impulse, just the love of the clothes and the pleasure of being a different person, in public.” She never crossdressed in private. “Underclothing held little interest for me.”

Felicity stood  6’2” (1.88m), but assumed that she passed, although others observed that she was usually read. She developed a reasonable contralto voice, quite different from her masculine baritone. She always tried on dresses in the shop. It is told that she went up to a policeman in Times Square pretending to be from Texas and got him to take her photograph.Zagria Cowart, 2011


Felicity, November 9, 1961, Inscription on back of the photo.

Felicity was always well put together and fashionable. Like many crossdressers, she was a fan of photos of herself, and she frequently posed in formal dress. She owned a variety of fur stoles and capes and wore them, often in hot weather. According to Zagria Cowell, she kept an apartment in New York City specifically for crossdressing. She was friends with Virginia Prince and put her up once in her apartment. Virginia was mugged during her stay.

Jan met Felicity when she joined the Mid-Hudson Valley Transgender Association, a support group. By that time she was unable to drive and attended only when someone was able to bring her to the meetings. Jan says, “I remember one evening when I got dressed at her home, attended the meeting, and came back to change at her home. I could see from the front door that she was asleep in the chair in the living room. I rang the doorbell, and she slept on. I knocked several times and couldn’t wake her up. She didn’t stir even when I pounded. I went around to the window by her chair and pounded on it, but she didn’t stir. I ended up going to my workplace to change. No one saw me and I was able to leave without a problem, but I certainly didn’t want to make this a regular occurrence!”

For the occasion of Felicity’s 100th birthday, her support group gifted her with a makeover. Afterward, she looked into a mirror and said, “Geesh, I can do this myself!”

In the more than two hundred photos we scanned from Felicity’s 1961-1962 photo albums, there were many images of her, but in the interest of brevity, we give you here only one; follow the link we provided above for lots more. Fortunately, Felicity made notes on the margins or backs of most of her photos; thus we know the dates and subjects for most images, and for some, the location.

Thanks to Virginia Prince’s Transvestia magazine, Felicity soon met other crossdressers in the New York area. Since the early 1950s, Marie and Susanna Valenti had hosted crossdressers at their apartment at 875 West End Avenue in New York City, and their Chevalier D’Eon Resort in the Catskill Mountains. Later, they would sell the property and buy another resort in nearby Hunter, NY which they called Casa Susanna. Recent discovery of photos from the Casa Susanna years resulted in a book, a Broadway play by Harvey Fierstein, a movie by French Director Sébastien Lifshitz, and many articles in the popular press—but Felicity’s photo books predate the opening of Casa Susanna by a couple of years.

Roster, the Playgirl Club, 1961.

Felicity’s albums center on the first two get-togethers of the Playgirl Club, hosted in Poughkeepsie, where she lived; and almost certainly at her house, as she hosted the meetings. Neither of us had heard of the Playgirl Club, which was probably short-lived, but some of the players show up later in the Casa Susanna photographs, including resort owners Susanna and Marie Valenti, noted science fiction author, member of the Futurians, and co-founder of Ace Books Donald A. Wollheim, and the one and only Virginia Prince.

11/12/1961, Playgirl Club, First Weekend House Party, Poughkeepsie, NY.

We’re certain many of the attendees of the Playgirl Club meetings can be found in the pages of Transvestia, Michel Hurst and Robert Swope’s Casa Susanna,  and collections of early photos

Here, Captain Miller has to leave the Playgirl Club’s First Party to Pilot an Airliner.

held by the Louise Lawrence Transgender Archive in Vallejo, California and The Transgender Archive in Victoria, British Columbia. Bobbie Davis of the Louise Lawrence Archive and Dallas have been working together to trace these linkages.

The materials Felicity and Jan took to the LGBT Community Center in New York are catalogued as the Felicity Chandell Papers and include personal correspondence, often with photos,receipts, newspaper clippings and comics, event brochures, newsletters, product catalogs, Tri-Ess directories, and early books on crossdressing.

We conclude with a few photos from Felicity’s Chandelle’s 1961 and 1962 photo albums. In addition to being one of the twentieth century’s most notable and well-known pilots, Felicity has gifted us with a significant piece of trans history.

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Category: History


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