For the last few days the Philip Mould showroom in London has been displaying a recently discovered portrait of the so-called “Patron Saint of Transvestites,” the Chevalier D’Éon. Dating from 1792 it is believed to be the earliest surviving formal portrait of a male transvestite though, at first, the painting was believed to be of a masculine-looking, middle-aged woman. Recent restoration and cleaning revealed a distinct five-o’clock shadow and further investigations concluded this was actually a documented portrait of D’Éon by the English theatrical painter Thomas Stewart, lost since 1926.

The life story of Chevalier D’Éon is fascinating and remarkable. After excelling at school he was recruited as a member of Le Secret du Rois, a network of spies who worked personally for King Louis XV. Stories of the Chevalier’s exploits as diplomat, spy, and master swordsman abound, including claims that D’Éon, disguised as a woman on a secret mission Russia, became one of the Empress’s maids of honour. It seems he could out-scarlet the Pimpernel himself.

In 1763, D’Éon was sent by Louis to London as a Special Ambassador. In fact, he was a spy. Despite documents proving he bought female corsets, at this stage D’Éon’s transvestism was a secret. When his job was given to someone else, he disobeyed the order to return to France and caused a scandal by publishing some of his diplomatic correspondence. Cleverly, he kept the papers pertaining to his spying mission and used them to blackmail the King into letting him stay.

It was at this point D’Éon began to dress publicly as a woman and no one’s really sure why. A betting pool was even started on the London Stock Exchange about the Chevalier’s true sex, though after a year during which no proof was available either way, the wager lapsed. Contemporaries described D’Éon as wearing elaborate female attire, but with masculine characteristics such as stubble and a habit of hitching up his skirts up when ascending stairs – it’s hard not to imagine a Little Britain sketch. 18th century society found it much more acceptable to class him as a masculine woman rather than a cross-dressing man and, actually, D’Eon took to describing himself as female, brought up as a man by his family in order to claim inheritance. The fact is, biological sex aside, the Chevalier spent the first 49 years of his life living as a man, and the last 33 years of her life living as a woman.

After the death of Louis XV, D’Éon negotiated a return to France. She kept her ministerial pension on the condition that she not only turn over the correspondence concerning Le Secret du Roi, but also that she dress in women’s clothing (to avoid any uncomfortable confusion I suppose). D’Éon agreed, especially when the king granted her funds for a new wardrobe and, in 1777, the Chevalier returned to her home town, having been banished from Paris.

Impoverished after the French Revolution, but still a celebrity, D’Éon returned to London in 1785 and took to the stage where she performed as a renowned female fencer in tournaments and spectacles until wounded in 1796. By 1805 she had spent a year in debtor’s prison. D’Éon’s last years were spent with a widow called Mrs. Cole, though very little is known about her sexual preferences and proclivities. A panel of doctors examined the Chevalier’s body after death and discovered that she was indeed anatomically male.

It’s possible that the National Portrait Gallery will buy this picture and, if it does, it will be the first painting of a cross-dresser in the collection (if you don’t count Maggi Hambling’s superb image of George Melly as Bessie Smith). But is it too simplistic to describe D’Éon as a male transvestite? I think it might be. Havelock Ellis, author of the first English medical text book on homosexuality, coined the term “Eonism” to describe a more complex form of cross-dressing gender play, and the word was in common use until quite recently.

The painting itself is finely executed and historically significant, not just because of the Chevalier’s incredible story, but because of the ambiguities the portrait contains.

There’s a softness around the blue grey eyes, a gentle tilt of the head, as was stylish in portraits for the time regardless of the subject’s gender, and a slight, playful smile on D’Éon’s lips. The dress and hat are fashionably simple – almost the 18^th century version of the little black dress. Whatever D’Éon’s sex, the Chevalier seems very comfortable with who she, or he, is.

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