As reported in The History Blog:
British art dealer and art detective Philip Mould... came across an arresting portrait of what appeared to be a rather masculine middle-aged woman. Named “Portrait of a Woman with a Feather in her hat” and attributed to painter Gilbert Stuart...
A thorough cleaning revealed that the artist was not Gilbert Stuart... Old varnish and dirt had obscured the signature of the real artist: Thomas Stewart, an 18th century English painter who is not very well known today...
The cleaning also revealed another telling detail: a noticeable five o’clock shadow on the lady’s face. Moira is known to have owned a portrait of the Chevalier d’Eon, and the Chevalier was known to always wear a black dress and the medal of the Order of St. Louis, which he had been awarded by Louis XV for his work as a spy...
Connecting all the dots points to this portrait being of Charles Genevieve Louis Auguste André Timothée D’Eon de Beaumont, aka the Chevalier D’Eon, a biological male who spent his first 49 years dressed as a man, fighting in the Seven Years’ War, fomenting political intrigue as part of Le Secret du Roi, King Louis XV’s personal secret spy network, and serving as Minister Plenipotentiary in London in 1763....
By the time he returned to England permanently in 1785, he was wearing women’s clothes full time. According to witnesses, he made no attempt to adopt feminine mannerisms. He hiked up his dress to run up stairs and fenced with manly vigor. Yet, the question of his sex was widely debated in society at the time....
When he was examined by a physician after his death in 1810, many people were shocked that his genitals were found to be intact and entirely male. The Chevalier d’Eon was so strongly associated with gender ambiguity that psychologist and researcher Havelock Ellis coined the term “eonism” to describe cross-dressing and other transgender behaviors...
Although prints of the Chevalier in a black dress wearing the Order of St. Louis medal are extant, this portrait is the only known oil painting of him. It may be the first formal portrait of a cross-dressing man wearing women’s clothing.
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