One of the anecdotes that tends to stick with students in my survey courses, to the end of the semester and beyond, is that trousers were largely regarded with derision in the Classical world. For the inhabitants of the Greek city states, and for the Romans of the Republic and the early Empire, trousers were ridiculous and effeminate, fit to be worn only by the barbarians of Persia and northern Europe. No honourable man would have worn a pair in public. This throwaway piece of information sticks with my students because it’s strange to them, and it’s strange because it conflicts with one of their most fundamental, internalised assumptions: that there are innately “male” and “female” modes of dress, and these are the ones with which they’ve grown up.

If certain recent media reports are accurate, these assumptions are widespread ones: Donald Trump has reportedly ordered the female staff in his administration to “dress like women” and has pressured them to wear dresses or skirts on the job. This has gone over about as well as you might expect. The hashtag #DressLikeAWoman has been trending on social media, with many women—doctors, pastors, soldiers, politicians and more—pointing out that the only way to “dress like a woman” is to identify as a woman and, well, put some clothes on.

A woman called Walpurgis (left) wields a sword in this illustration from a ca. 1300 manuscript. Leeds, Royal Armouries Ms. I.33 f.32r.

It would be easy to dismiss this as a silly squabble about expectations of professional dress, but the #DressLikeAWoman debate is just the latest expression of deep-seated cultural anxieties about how women should visibly express their gender identity. It’s a conversation that has medieval antecedents. Texts and images from the Middle Ages show that then as now, clothing could make the woman—or potentially unmake her, if she transgressed contemporary expectations for how her gender should dress.

Clothing, hairstyles and accessories were all gendered in the medieval period, and yet women cross-dressing as men is a trope that appears frequently both in cultural fantasy and in actual practice during the Middle Ages, as women tried to pursue opportunities otherwise closed to them. There are several “transvestite saints” from Late Antiquity, women who assumed a male identity in order to enter a monastery. Theodora of Alexandria dressed as a man so she could become a monk in fifth-century Egypt. Marina, most likely from what is now Lebanon, shaved her head, donned male clothing and the name Marinus, and lived an ascetic lifestyle for many years with her brother monks. Though falsely accused of fathering a child with a local woman, Marina’s biological sex was only discovered after death and she was acclaimed for her holiness. Marina, Theodora, and the other “female men of God” were highly popular saints throughout the Middle Ages—praised by many as women whose holiness was made manifest through their denial of their femaleness and who had overcome the apparent limitations of their sex.

St Marina, dressed as a monk, kneels before an abbot and several monks, while inside the building her father lies on his deathbed. New York, Morgan Library, MS M.672-5 III, f. 279v.

This doesn’t mean that women wearing men’s clothing met with universal approval in the Middle Ages. Then as now, opinions were not monolithic and could even be contradictory depending on context. Patristic figures like St Jerome and later ones like Bernard of Clairvaux vehemently defended the importance of gendered distinctions in dress. Sumptuary legislation enacted during the Middle Ages defined clothing according to gender, age, and social class. Dressing in ways that defied such norms could be dangerous, but women did so anyway.

The medieval cross-dressing figure likely best known to modern audiences met an unpleasant end: Joan of Arc, the fifteenth-century French teenager who claimed prophetic visions, participated in military campaigns, and was eventually burned at the stake in 1431. Yet what is perhaps less well-known is that Joan was, strictly speaking, not executed for her political or military activities, but because she was convicted of  heresy—because she claimed to hear angels and because she wore male clothing. In her trial, she was accused of  wearing her hair “like a young coxcomb” and, by wearing “the garments of a man, short, tight, dissolute”, defying “Divine Law”. She carried and used weapons, something that wasn’t socially acceptable for women. In doing these things, according to the church, Joan of Arc committed blasphemy. Unlike the transvestite saints, Joan didn’t succeed in “transcending” her sex. This may have been because she dressed like a man but insisted firmly on her femaleness and referred to herself as la Pucelle, the Maiden. Joan of Arc was publicly female and yet, perhaps, just as publicly not a woman. For her contemporaries, this was a serious problem.

This 15th century miniature shows the biblical Judith (left) holding the head of Holophernes and Joan of Arc (right) holding a spear. From Martin Le Franc, Le Champion des Dames. Paris, Bibliothèque nationale, MS Français 12476, f.101v.

These examples of cross-dressing and gender transgression in the Middle Ages can be multiplied: the case of John/Eleanor Rykener, an English sex worker from the late fourteenth century who has variously been interpreted as transvestite or transgender; the fictitious Pope Joan, who was said to have ascended the papal throne in the ninth century claiming to be a man and whose deception came to light when she gave birth during a religious procession; Silentius, the main character of the Roman de Silence, a thirteenth-century romance in which a girl is raised as a boy and becomes a skilled knight. Taken singly or together, these accounts and many more are illustrative of how unstable gender can be even when it is presented as something innate and inviolable. They show that people have long been willing to transgress, break, redefine, or ignore gendered boundaries—and to punish one another for doing so.

They also underscore the fact that the dress code allegedly being implemented in the White House is nothing more than a regulatory fiction. Any attempt to make womanhood dependent on conformity to an arbitrary set of standards ignores the fact that if you want to #DressLikeAWoman, you’ve got a very big wardrobe to choose from.