As I note below, I originally picked this up because I thought it would cover all types of cross-dressing in the context of chivalric romances and tournaments. But even though it's restricted to contexts where men perform femininity in a public context, it's still quite relevant to understanding medieval attitudes toward gender crossing and gender performance. In particular, it's a strong reminder that men and women lived in entirely different universes with regard to how cross-gender performance and gender transgression were received.
Putter, Ad. “Transvestite Knights in Medieval Life and History” in Cohen, Jeffrey Jerome & Bonnie Wheeler (eds). 1997. Becoming Male in the Middle Ages. Garland, New York. ISBN 0-8153-2836-2
[Note: I originally picked this up thinking that it would cover literary female cross-dressing knights as well as male ones. Although the article is entirely about men cross-dressing as women, it helps to round out the picture of how medieval people viewed clothing as a gender signifier and some of the asymmetries of cross-gender behavior.]
Putter looks at the phenomenon of (male) cross-dressing knights, both in historical records and in chivalric romances and considers how the topic contributes to our understanding of gender and sex categories in the middle ages.
A key starting point is an understanding that--then as now--gender was a performance and one only tangentially connected with physiology. The official position on cross-dressing, both from the law and from moralists, was condemnation and persecution, which makes it all the more startling to find cross-dressing as a regular motif in medieval romances and even in real-life tournaments. Male cross-dressing is often, though not always, used for humorous purposes or to demonstrate power dynamics. But at a more basic level, the use of gender disguise in these contexts, rather than undermining the distinction between the sexes, is used to emphasize it. The chivalric cross-dresser is not necessarily a directly comic figure, but is typically placed in a context that safely contains his transgressive potential and diverts it to humor.
Social prohibitions on cross-dressing took their authority from the Bible: “The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman’s garment” and this was taken up in secular law codes in the first millennium, as well as in treatises of religious philosophy. But concerns around clothing and social categories were not limited to gender. There are parallel concerns about using clothing similarly to blur the distinction between the clerical and secular worlds. Transgressions of multiple types of categorical distinctions were often mingled in the same contexts.
The condemnatory tone around cross-dressing had two significant exceptions. Men were allowed to portray women on stage during those eras and cultures when it was considered inappropriate for women to be actors. And women were forgiven temporary instances of gender disguise for the purpose of protecting their chastity, especially in order to escape marriage to enter a religious life. (The female “transvestite saints” were a special case of this.)
In general, there was more tolerance for women disguising themselves as men due to the relative social status involved: it was more understandable for women to “elevate” themselves to men, than for men to “degrade” themselves as women.
Examples of male cross-dressing in ordinary life are extremely rare, which makes the motif of the cross-dressed knight all the more curious. What was it about this context that allowed for crossing gender boundaries in this way?
One major factor is that the cross-dressing occurred in the context of tournaments--an activity focused on the performance of extreme masculinity. And in the middle ages, tournaments themselves because quasi-theatrical performances, modeling themselves on the tournaments described in chivalric literature. An example would be a tournament held in 1286 to celebrate the coronation of Henri II of Lusignan as King of Jerusalem. As one chronicler notes, “they imitated the Round Table and the reign of Femenie, that is, knights dressed as ladies, and they jousted together. Then they played nuns that had with them monks and they jousted with each other; and they impersonated Lancelot and Tristan and Palamedes, and played many other splendid, delectable, and pleasinge games.” That is, the knights jousting in the guise of women were playing fictional roles, just as they did when taking on the personas of Arthur’s knights.
A similar diversity of disguises is seen in the life of the famous 13th century Bavarian knight Ulrich von Lichtenstein, who took on the personas of King Arthur and Lady Venus at different tournaments, and inspired others to take on similar roles, crossing gender and clerical lines. The boundary between tournament and theatrical role-playing is more blurred in a performance reported from the marriage feast of Edward I of England and Margaret of France, which involved one of the king’s squires impersonating the “Loathly Lady” of Chretien’s Perceval.
When pieced together from various sources, the phenomenon of chivalric cross-dressing is seen to be surprisingly common, as if one counts “crossing” that includes not only gender boundaries but crossing between social classes (knights vs monks) and crossing between the world of reality and that of myth or legend. In turn, the popularity of this sort of real-life chivalric cross-dressing may have inspired or popularized the use of the motif in chivalric literature.
In a literary context, transvestism is somewhat more likely to be done in a context of mockery, as in the Tournament of Surluse when Sir Dinadan’s reputation for jokes is turned around on him by Lancelot who appears on the tournament field disguised as a maiden, as if to be the prize of the combat. The disguised Lancelot then charges Sir Dinadan and unhorses him. Dinadan’s shame at being defeated by “a maiden” is compounded when he is forced to wear a woman’s dress on his return to the court.
This is the contradiction of chivalric transvestism: as long as a knight engages in it voluntarily, it doesn’t affect his masculinity or reputation, in particular, if he does so in the context of “proving” his masculinity by victory in a tournament. The tournament context creates a presumption that all participants are male, thereby undermining the subversive nature of cross-gender play. Moreover, the more general practice of semi-theatrical disguise in the context of tournaments, undermines the specifically gendered aspect of putting on female garments. These theatrical displays also typically have “unmasking” as part of the climax, reaffirming the essential masculinity of the knight. What the author proposes is that in both chivalric romance and actual tournaments, knights “prove” that they are not women specifically by pretending to be women and then contradicting it, both by deeds and by a public revelation of male identity.
Further, the association of female identity with “performance” and artificiality creates a contrast with the “naturalness” of male identity. As in Raoul de Houdenc’s 13th century Arthurian romance Meraugis de Portlesguez, it is right to mock and punish those who are deceived by the gender disguise, for the “reveal” demonstrates the truth that was always present under the disguise.
The negative side of gender disguise in romances is seen in the motif of the man who uses it to gain sexual access to an otherwise-forbidden women. [Note: the roots of the “trans women are invading your bathrooms” motif run deep.] This is seen in the 13th century fabliau Trubert where the protagonist disguises himself as his sister to deflower the Duke of Burgundy’s daughter, or in several other romances: the Vulgate Merlin, the Roman de Silence, the Prose Tristan and others where men are disguised as handmaidens or nuns to have unquestioned access to a (consenting) noble woman for sexual purposes.
One other literary context for cross-dressing is mentioned in the footnotes to the article. In Arthurian romance, the role of messenger is normally assigned to women. Male strangers entering the court are framed negatively. The general rule is that a female visitor is a messenger but a male visitor is either a challenger or a prisoner. Within this context, knights are depicted specifically as dressing up as a “messenger girl” in order to be met with acceptance rather than hostility.
The same-sex erotic potential of gender disguise is introduced more rarely. In the 13th century romance Witasse le Moine the cross-dressed hero has to fight off the amorous advances of another man (and the narrator feels the need to reassure us that our hero is not a “sodomite”). A similar episode occurs in the 13th century romance Claris et Laris where the hero is magically changed into a “maiden” until he can find the two best knights in the world. But unlike episodes where a change of body results in a change of desire (as in Tristan de Nanteuil), he retains heterosexual male desires while in the maiden’s body and fights off male sexual assault.
Real-life examples of men cross-dressing as women outside of a tournament/theatrical context are rare in the record. The most notable English exception is the 14th century case of John Rykener who was taken in custody as “Eleanor” on suspicion of prostitution. (The law seemed at a loss to figure out what Rykener’s offence might be once the gender disguise aspect was apparent.)
In literary contexts, the potential for male same-sex interactions was raised only for the purpose of vehemently denying it, often violently. More often, the potential is not raised at all and the cross-dressed figure is either the perpetrator or butt of a joke. (The article goes into some detail on the theoretical analysis of transvestite-centered humor.)