A serious student of moral turpitude, teenage Caligula studied sexual excess on the isle of Capri, mentored by his uncle Tiberius, then Roman emperor. The young man was both a voyeur and the object of his uncle’s ingenious depravity. When Caligula learned that he became sexually aroused by cruelty and torture to others, he tried on every perversion he could manage.
During those formative teen years, Caligula often cross-dressed, preferring blond wigs and long robes. He adored clothes, especially the expensive, clingy garments that women wore, made of Koan silk. An army brat who’d moved often with his family, Caligula had caught sartorial mania early. While he was a wee boy living at the military outposts of his father Germanicus, his mom had dressed him in soldier’s kit, including a child-size pair of the legionary’s classic footgear: sandals with hobnail-covered soles calledcaligae. Soon the bored-senseless soldiers nicknamed the kid Caligula, meaning “little boots,” or (to be precise) “little hobnailed sandals.”
A dedicated sadist and an occasional transvestite, Emperor Caligula terrorized family, friends, and Romans throughout his four-year reign.
As time went on, Caligula managed to sexually abuse his three sisters and quite a number of other innocent folks. Once he became emperor in A.D. 37, his real forte was one-upping rivals, nonrivals, and anyone else who came into his presence. With Caligula, sexual pleasure was inextricably linked with punishment, the more vicious the better.
Afflicted with mental illness that ranged from delusional to manic, the emperor often failed to sleep at night. He frequently put on extempore dramatic and musical performances during those insomniac hours, ordering his top aides and family members to be his adoring audience. Those witnesses who managed to survive the random killings and maimings that Caligula routinely dished out on a daily basis no doubt remembered the remarkable ladies’ attire the emperor wore during those memorable nights.
Nero, who as a small boy spent time in Caligula’s tender care, was very impressed by his uncle’s style. In fact, when Nero became emperor twenty-plus years later, he emulated Caligula’s fashion sense, often dressing as a woman as well. His favorite gear to wear to dinner was called a synthesis, the flowered gown worn by men only during the Saturnalia festival each December. Otherwise, the synthesis was female garb. Nero tried hard to make it a new trend in Roman fashion, but in vain, apparently.
Nevertheless, as emperors came and went, there were ardent cross-dressers among them, such as Elagabalus, whose purple gowns and painted eyes drew much attention. A figure of fun and an object of Roman disgust, this young emperor had a real desire to be female, not just look like a dame. As emperor, he seriously explored the possibility of sexchange surgery with his doctors. A man well ahead of his time, Elagabalus asked them to create for him a prototype of a female vagina! Pretty daring stuff, given the surgical abilities and the paucity of anesthesia in those days. The doctors managed to decline without incurring imperial wrath.
In ancient times, cross-dressing occurred for multiple reasons—many times it wasn’t a gender statement. For example, women occasionally had strong motives for dressing themselves as men. Greek philosopher Plato, although he disparaged the minds of women as inferior, did accept two young women named Axiothea of Phlius and Lasthenea of Mantinea as students. They wore what the other male students wore; more about them we do not know. They received a passing mention in Diogenes Laertius’s Lives of the Philosophers.
Other women, such as Thecla, the assertive and determined sidekick of Paul of Tarsus during his wanderings on land and sea around the Greco-Roman world, adopted male garb for safety. She remained his staunchest disciple for years.
Still others cross-dressed so they could take part in activities declared taboo for women. Such was the case for Pherenike, the Rhodian mother who acted as boxing trainer for her son in the Olympic Games of 388 B.C. (You’ll find her story in the entry on Pherenike of Rhodes.)
Of even more ancient vintage, Hatshepsut, the female pharaoh of Egypt during the eighteenth dynasty, ritually dressed in male regalia to legitimize her reign, even though it was through the female bloodline that pharaohs became heads of state.
In seventh century Mesopotamia, Ashurbanipal, the Assyrian ruler famed for creating the world’s first great library, appears, like Elagabalus, to have been a true cross-dresser, a man with transgender longings. Although married to a redoubtable gal named Ashursharrat, he chose to wear female clothing and accoutrements. He also used a major amount of cosmetics and imitated a female voice as he spoke. All of this vastly irritated other Assyrian men, including one of his generals, who happened to walk in when Ashurbanipal was penciling his eyebrows. Pulling out his dagger, the general ran his boss through on the spot.