The "Chevalier D'Eon," a 18th-century painting of a cross-dressing man, who may have identified as female at one point, recently sold to a British gallery.
The painting, by Thomas Stewart, depicts Chevalier D'Eon, who apparently lived quite a life of intrigue as a British-based employee of King Louis XV's secret service. It's believed D'Eon began dressing as a woman to evade capture after betraying the French government, eventually identifying as a woman until dying in 1810.
It was only recently revealed, thanks to restoration, that the Stewart painting portrayed a biological man in women's clothing, instead of simply a biological woman. Ever since the British National Portraits Gallery purchased the painting from a New York dealer, the portrait has attracted much curiosity. It's believed to be the earliest found painting of a gender-ambiguous person. Read more here.