This essay is one that has been percolating for a while in my mind. I originally posted it on Live Journal, but since it intersects with a project that I've been planning to create for my website, it seemed useful to post a copy here as well.
Introduction and Disclaimers
Some time ago, I gave someone on Live Journal a promissory for an essay about my own personal take on women cross-dressing in the SCA. And I made some initial notes and started a draft and then it fell off the priority list. And then the topic came up again in a discussion at a local sewing circle and I worked on the essay some more. And then it fell off the priority list. But since it's a theme that I find interesting both on a personal and sociological level, I kept plugging away and came up with this essay.
But this being me, I couldn't leave it at just talking about my experiences and attitudes. No, I had to put together a review of the literature, a typological analysis, and a technical vocabulary for the distinctions I'm trying to make. (The literature review isn't intended to be exhaustive -- it's simply what I had lying around the house.) So I'm going to start with a discussion of some of the roadblocks modern people have to understanding some of the historic attitudes and dynamics, then cover a brief survey of some types of cross-dressing found in medieval and Renaissance Europe. From this I'll attempt to extract a gross classification of types and purposes of cross-dressing in this period of history and then compare and contrast it with the types and purposes that I've observed in the SCA. Only then will I talk about how the cross-dressing that I do in the SCA fits into this overall picture.
A few ground rules to begin with. I'm not going to talk about men cross-dressing. It's not something I have a personal interest in, and both the historic and contemporary context are enormously different from the female case. It's an entirely separate subject. Secondly, I'm not going to address clothing issues relating to modern people who identify as female-to-male transgender. Not only do I not have the background to speak knowledgably on the topic, it moves away from my main exploration of clothing use in modern culture and in the SCA as voluntary personal expression. I do acknowledge, however, that some of the historic examples of female cross-dressing that I'll be talking about have very fuzzy boundaries with transgender issues. We not only can't always know how historic individuals understood their own actions, but they had entirely different sets of mental categories that they were evaluating themselves against. In not talking about possible transgender issues in history, I don't mean to erase that possibility, but simply to view the historic evidence from angles that are relevant to my modern topic.
The Modern Context
I think a 21st century audience may sometimes have trouble putting pre-modern attitudes in context without having a sense of how very recent the loosening of strictly gendered clothing rules are. So it can help to work our way backwards through changing 20th century attitudes. A lot of these changes are still fresh in memory. When I was in high school in the mid '70s, girls were still forbidden to wear pants to school (at most schools -- rules were on the cusp of change, and the change happened in different places at different times).
As late as the mid 20th century there were laws on the books in California (just to pick a context for which I have references) that criminalized the wearing of clothing associated with the opposite gender. [Faderman & Timmons 2006] These laws were, of course, enforced very selectively. A woman of solidly heterosexual credentials wearing Levi's and a plaid shirt during leisure activities wasn't likely to be harassed for it, but a working-class woman with short-cropped hair enjoying herself in a bar of questionable reputation might find the anti-cross-dressing laws used as an excuse during a police shake-down if no other infraction were evident.
The wedge that opened over the course of the 20th century to move trousers and button-down shirts and tailored suits and whatnot from being solidly male-gendered to being largely gender-neutral often began with "active wear" and then infiltrated more general contexts. Sporting activities were one avenue -- for that matter, there was a centuries-long tradition of women's riding habits borrowing from and imitating masculine styles. And the tendency for sports clothing styles to trickle down from the upper classes (the people who have the resources and desire to devise specialized clothing for leisure activities) meant that the styles came with an inherited "protection" from disapproval associated with that class. Even so, you can see lingering expectations that women participating in sports will wear "girly" clothing in the absurd costumes sported by figure skaters and tennis pros.
The second avenue for masculine-derived "active wear" infiltrating the acceptable styles for women was through working clothing designed for safety or practicality in "male" occupations. Rosie the Riveter got a pass for wearing coveralls because she had already been given a pass for taking "a man's job". It was harder for a society that had begged women to take on male-dominated jobs (and their attendant clothing styles) for the good of the country to turn around and claim that those styles were inherently unwomanly once the industrial need was past. (They tried, but it was harder.)
Somewhere in between the two avenues was women's use of "mannish" clothing as an intentional signifier when infiltrating a traditionally masculine field such as academia or management roles in business.
But the status quo that made these transitions notable was clear and explicit: In Western cultures, before the later 20th century, clothing was defined by gender and gender by clothing. Crossing that line was a Big Deal and doing so openly had major social and legal implications. So let's skip back to the medieval period and look at some of those attitudes and consequences.
The Medieval Context
In medieval Western culture, pants were a masculine garment. No question. End of discussion. In medieval art and literature, even the wearing of underpants by women was used as a symbol of the usurpation of masculine social power and privilege (usually at the expense of some particular man). [Moxey 1989] And this was only the most extreme end of the scale for gender-marked clothing. Apart from the significance of particular garments, there were many stylistic elements of clothing that were clearly gendered. While early medieval garment styles often seem fairly unisex to our eyes (with the exception that women's hems were obligatorily long), especially with the rise of more highly tailored clothing styles in the 15th century and later, the styling and cut of garments became strongly gendered.
Given this clear distinction between male and female clothing, medieval literature (including hagiography) is surprisingly rich in examples of female cross-dressing. But when pursued to their roots, these motifs that appear to transgress the norms of clothing gender actually serve to emphasize them.
Female saints whose legends included cross-dressing follow several stereotyped patterns. In one group, the woman cross-dresses to escape from an unwanted marriage in order to take on a virginal religious profession instead (but most commonly involving resuming life as a woman). In another group, the woman chooses to pass as a man in order to live a monastic life (at a time prior to the establishment of female orders). [Anson 1974, Hotchkiss 1996]
Similarly, the heroines of romance, such as Silence and Yde [Roche-Mahdi 1992, Clark 1998], who take on male attire do it not to appropriate male roles and activities as women, but to escape the hazards and vulnerabilities of womanhood by erasing their female gender and substituting an entirely masculine presentation.
The common theme in these stories is that of using crossdressing to completely change the interactional gender of the wearer. These aren't cases of "wink wink, nudge nudge" where everyone knows it's a masquerade. The point is to remove the social and physical hazards of being female and to gain the social advantages of being male. In the stories, the masquerade is completely successful up until the point when the plot requires disclosure. How realistic was this? We'll get back to that question.
Much rarer are literary motifs where the transvestism is overt and acknowledged within the context of the story. The examples that come to mind are set "long ago and far away", like the story of Semiramis as re-told in Boccaccio's De Mulieribus Claris [Brown 2001], or the character of the Amazon Bradamante in Orlando Furioso[Bullough 1996]. One exception is the genre of "maiden warrior" stories in Germanic and Old Norse literature where a daughter who, through mischance, is the sole heir to a heroic lineage, is raised as (or assumes the role of) "substitute son", taking up arms, wearing male clothing, and usually taking on a masculine name. [Clover 1995]
On the historical, rather than literary side, the rare cases of open cross-dressing similarly point out how far outside acceptable society a woman placed herself by doing so (or how far outside acceptable society she had to be for cross-dressing to be discounted as among her lesser crimes). Joan of Arc may have begun cross-dressing as a practical matter, but it became a major point of contention when the English court was looking for specific accusations to make against her. [Hotchkiss 1996]
The early 17th c. Catalina de Erauso had a history worthy of the most implausible persona back-story: born of a noble Basque family, when on the verge of taking vows as a nun, she ran away from the convent, put on man's clothing, and became a soldier in the New World where she passed as a man for 20 years. When her biological sex was revealed, her story and military deeds made her such a media sensation that she received permission (from the Pope, no less) to continue cross-dressing. [De Erauso 1996, Velasco 2000]
During the same general era in England, Mary Frith (aka Moll Cutpurse) established open cross-dressing as one small part of a tabloid-worthy life of criminality and outrageous public behavior, performing a balancing act between sufficient excess to be entertaining to the masses (and thus granted some tacit license) yet not so much that Something Had To Be Done. [Todd & Spearing 1994]
Given that this historic record is only going to tell us about the failure points in attempts to "pass", how realistic is it to suppose that a cross-dressing woman in a pre-modern culture could entirely and successfully pass as a man on a long-term basis? We know that it was possible, and in fact some passing women were discovered only after death. Decker & van de Pol (1989), studying over a hundred Dutch cases from the 17-18th centuries, found that when the information on duration was available, a quarter succeeded in their masquerade for less than a month, another quarter for 1 to 6 months, and half for over 6 months up to some cases of a decade or more.
The context in which we start seeing systematic and non-exceptional evidence of passing women is when significant migration made it possible to leave behind one's previous life and to establish a new life, necessarily as a complete stranger with no pre-existing social ties. Migration to the more anonymous urban environment also enabled passing in a way that a more constrained, less private rural life did not. Perhaps surprisingly, the military and the close quarters of naval life turned out to be a fertile ground for successful masquerade. And those real-life experiences of passing gave rise to new motifs in popular literature of the "saucy sailor-boy" type, although the literary motifs probably contributed more to the modern image of historic cross-dressing than the reality did. [Cressy 1996, Dugaw 1996]
A Digression on the Mechanics of Passing
One key element probably needs to be emphasized to the modern reader. To pass as a man, a woman largely needed to recreate her life from scratch. Every person who knew her "before", every potential intersection with her prior life, increased the risk of exposure. In our modern world of constant migration, "self-made" lives, and the mythologization -- nay, fetishization -- of the "lone wanderer" motif, it's easy to lose sight of the importance of family and social networks to mere existence (to say nothing of a comfortable life) in pre-modern times.
So if you, as a modern person, want to contemplate the practical hurdles faced by a woman passing as a man in medieval society, imagine yourself transported to a small rural town -- one that fits all the stereotypes of being suspicious of "outsiders" -- with next to no money, no job, no job references, in fact, no possibility of providing any documentation of your prior existence, like a driver's license or credit record or resume. What sort of job are you going to get? What sort of living arrangements? Are they ones that will allow you bodily privacy? How will you answer questions about your past? How much personal curiosity and scrutiny will you experience? Will you be picked as a scapegoat because you're a stranger? How will you deal with that? If you have to leave town in a hurry for your own safety, what can you take with you? (Probably not any wages owed to you. Possibly nothing except the clothes on your back.) Now start all over again in the next town with what you have left (and the possibility of someone from the previous town coming through and recognizing you).
I'm digressing quite a bit here, but I'm trying to emphasize how non-trivial the decision to pass was.
But conversely, in terms of the functional success of cross-dressing in order to pass, the very taboo against casual cross-dressing increased the likelihood of success. In the modern world, we take it for granted that someone wearing even the most essentially masculine clothing (e.g., business suit and tie) might be female. And so we are alert and sensitive to other gender cues, from body shape and facial skin texture down to examination for an Adam's apple or tell-tale bulge at the crotch. We accept that a woman may wear male-gendered clothing (even that narrow scope of clothing that hasn't become functionally unisex) without intending to pass as a man, so it's socially necessary to use these other cues lest we commit a social faux pas.
But in a culture where the casual adoption of male dress by a woman is less thinkable, the observer is less likely to look beyond the obvious gender category conveyed by the garments. If women don't dress like men, then if it's dressed as a man, it is a man. This sociological blindness wasn't entirely reliable. In the case of a 15th c. Polish woman who passed as a man for two years in order to attend the university at Krakow, she was discovered when a random soldier grew suspicious enough at her presentation that he made a bet with his companion regarding her true gender. [Shank 1987]
The point of all this historic review is by no means to argue that female cross-dressing did not occur or was vanishingly uncommon, but rather to emphasize that in actual everyday practice it was not done trivially or easily, and that "open" cross-dressing does seem to have been rare and unusual.
One specialized case of open cross-dressing is the theatrical portrayal of one gender by the other. Most people are familiar with the Elizabethan use of young male actors to play female roles (leading to an extra layer of humor and innuendo in the gender-disguise comedies). The reverse case -- women playing male roles on stage -- arose somewhat later, but famous 19th century examples include Sarah Bernhardt and Charlotte Cushman. Less familiar is the early history of female singers performing in "trouser roles" (en travesti) in opera. As Blackmer & Smith (1995) detail, well before the phenomenon of women replacing castrato roles beginning in the 18th century, many early operas were designed with "flexible" voicing where many major roles were written with options for either male or female voices to sing roles in both genders. The earliest example cited is Claudio Monteverdi's 1607 Orfeo.
In the absence of an intention to pass or masquerade as a man, women might sometimes adopt individual garments or accessories that were culturally coded as male. Because this type of partial cross-dressing was necessarily overt, it was inherently transgressive. In the Norse Laxdœla saga, the pretext for divorcing a woman is that she is "always in breeches" like a man. [Jesch 1991] Her motivation for wearing this garment (or even confirmation that the accusation is true) isn't given but the implication is that her offense is intruding into male territory. In the reported case of Queen Elizabeth wearing armor to rally defense against the Armada, the adoption of male-coded items was explicitly presented as symbolizing her claim to male-associated military power.
One interesting topic for tracing the appropriation of male-coded styles in post-medieval clothing is in the development of women's riding habits -- a field where there was a tacit license for women to adopt certain masculine sartorial features (at least above the waist), as well as an overt connection of this adoption with gender transgression, with references to the women so clad as "Amazons" and the like. [Blackman 2001]
A Thematic Summary of Historic Cross-Dressing
To recap the historic context (up through the 17th century or so), one can look at the phenomenon of women cross-dressing either from the point of view of an observer, or from the point of view of the woman's own motivation. By definition, to an observer, a successful "passing" woman should be perceived as indistinguishable from a man -- perhaps a youthful or effeminate man, but not necessarily. In contrast, if the intent is to present a comprehensive and consistent facade of a man, but the viewer both knows and is meant to know that the presenter is a woman, then we have what might be termed an "overt masquerade". This covers the theatrical case of en travesti and perhaps certain literary cases such as the Norse "maiden warrior". (Note that here we're talking about the observer's perception and knowledge, not about the purpose or function of the cross-dressing.) The third category would be the use of particular items of male-coded clothing without an attempt at complete masquerade. And the fourth general category (keeping in mind that these categories may shade into each other) would be the application of male-coded styles to female garments (as with the use of masculine elements in women's equestrian outfits).
The purposes for which women used cross-dressing similarly fall into some identifiable categories, but in this case we must remember that any particular woman may have had multiple purposes -- and some purposes may leave more solid traces in the evidence than others.
One clear purpose -- especially for short-term passing -- was protection from the hazards and vulnerabilities of being female. In disguise, a woman could more easily travel alone without question or without the fear of sexual assault.
As a longer term proposition, passing as male not only offered some physical protection, but could also create access to economic or social opportunities that were more available (or only available) to men. In literature -- perhaps less so in real life - this might be access to social status (e.g., as an heir). More often it could mean access to certain occupations or activities that were normally restricted to men. In some circumstances, this access to social or economic opportunities might be available via an open masquerade as well as through passing, as in the literary case of "maiden warriors" or the occasional motif (whether literary or allegedly historic) of women putting on men's clothing and armor in order to participate in tournaments.
The appropriation by a woman of male-identified social or legal power could be accompanied by some degree of male-identified dress. (I make a distinction between this and the prior category in whether the purpose is to "become" a man in order to be able to do something or whether the purpose is to symbolize that one has taken on "male" power as a woman by also using male clothing.) An example of this would be the legend of Queen Semiramis or the folk motif of a domineering wife "wearing the pants". One could also see the masculine (and particularly military) influences on women's equestrian clothing as falling in this category if one presumes that horsemanship was seen as being inherently "masculine" to some degree.
Passing could be done with the intent of filling a "male" role in interpersonal relationships. (I focus here on romantic/sexual relationships, but other gender-defined roles could be covered.) While there was occasional acknowledgement of the possibility of female-female romantic and sexual relationships, it was far more common for such relationships to be framed in a heterosexist paradigm (even by the participants) necessarily involving a "male" and "female" role. This framing can make it difficult to distinguish between what we today would characterize as a butch-femme lesbian relationship and a nominally heterosexual relationship in which one partner is a female-to-male transsexual. (As previously noted, this essay is not intended to cover transsexual experiences and interpretations, but neither do I want to deny the areas where both interpretations are supportable.) I don't want to get into the whole question of whether such labels are meaningful in a historic context at the moment, particularly since the underlying focus of this essay is on modern practices.
This "role-filling" purpose intersects with the gendered-occupation purpose (perhaps with a bit of economic need as well) in the case of theatrical cross-dressing.
These last two groups raise questions of one of the less knowable purposes. To what extent did women in history cross-dress for the purpose of what might be bluntly shorthanded as "titillation"? Here we must confine ourselves to cases where at least one observer is aware of the contradictory juxtaposition of female body and male signifiers (even if the general public is fooled). For example, if two women are romantically inclined, might one motivation for one of the pair choosing to pass (rather than finding some other accommodation that would enable their relationship) have been a positive esthetic preference for the idea of a woman in male clothing? (Above and beyond the social freedom to take on the social status of married couple?)
In the case of theatrical roles en travesti where the contradictory juxtaposition is not only known to a specific observer but to society as a whole, the speculations regarding attractions and motivations can get even more convoluted. If a man is titillated by a female performer en travesti, is he attracted to a woman but with the frisson of transgression lent by her appearance as a man? Is he indulging in attraction for a man with the option of claiming, "But she's really a woman"? And conversely, for the female admirer, is she guarding her attraction to a woman with the excuse that she's playing to the role? Or is she attracted to the male facade but with the safety net that her virtue isn't in danger? It would be an interesting topic to dig up further evidence on, although the phenomenon falls mostly outside the pre-1600 period in any event.
Cross-Dressing in the SCA: A Survey of Possibilities
In addition to the inescapable fact that women who cross-dress in the SCA (and their observers) are informed by 21st century culture and attitudes, there are some structural differences to the dynamics of cross-dressing that arise when we introduce the element of persona.
There are a wide range of approaches to persona. It may be approached as a seamless and complete presentation. It may be an "organizing principle" but not intended to be a continuous interactional performance. It may be more or less an arbitrary label that has little relationship to the presentation. What I'm contrasting here is not so much the success of the various types of presentation, but the intent behind them.
Persona and the logistics of SCA interactions in general add a couple more layers to our observer-based categories of cross-dressing. This historic category of "passing" probably needs to be split into "full passing" where a modern casual observer is intended to be deceived, and "nominal passing" where the observer isn't necessarily intended to be deceived but is signaled to treat the masquerade as successful. We can keep the category of "overt masquerade" where the observer is intended to understand "this is a woman dressed as a man and it's ok to acknowledge either role" as well as the categories of "appropriated male garments" and "male-influenced garment styles".
But when we look at the possible purposes and motivations that women have when cross-dressing in the SCA, that's where the complications really set in. Because not only do we add in modern attitudes towards clothing and gender roles (and several more centuries of history in which those attitudes developed), but we add in another layer of potential interactions. In the historic case, an observer interacting with a cross-dressing woman could potentially be interacting with the underlying person or with the surface presentation. In the SCA, between those two, we add in the persona. (And, for that matter, there's the complication that the observer may also be operating from any of these three layers at any given time. But we'll leave that part aside for the moment.) To shorthand these layers in the following discussion, I'll label them "person", "persona", and "presentation", and in all cases we're starting with the assumption that person=female.
Non-masquerade portrayals (persona = male, presentation = male)
This category covers cases where there is no intent to portray a gender-transgressive presentation but simply to create a male persona acting as a man and intending to be interacted with as a man. In certain ways, if a modern woman wants to participate in certain historic roles or activities and to do it in a historically informed way, this can present the fewest contortions or distortions of history to work around. (That is, I'm not saying that it's a distortion of history for women to have participated in those roles or activities either by passing or by challenging gender norms, just that these are necessarily "marked" cases.)
The degree of rigor with which the "presentation" is made can be highly variable. While audience-oriented historic re-enactment groups may place a strong emphasis on the success of the presentation, the more experiential focus of the SCA leaves more latitude for the "nominal" approach (i.e., where the visual/behavioral presentation is less successful but the intent is for it to be accepted as successful). This can be viewed as directly comparable to personas with an obvious mis-match in ethnicity between the person and the persona -- an extremely common phenomenon in the SCA and one that is generally accepted as normal. Following this parallel with ethnicity mis-match, we can see that the category (in terms of intent) also covers cases where where there is relatively little emphasis on a successful presentation (e.g., no attempt to conceal body shape) but there is a clear statement to the effect of "this is a male persona, please interact with me as such".
Persona-driven portrayals (persona = female, presentation = male or male-signaled)
In this category the purpose is to represent cross-dressing that an actual historic woman might have done for historic purposes. And as in the previous context, the presentation may be attempted as a fully "stage-worthy" portrayal, or may be a nominal (yet consistent) attempt, or may be signaled symbolically or partially. (This raises the question of why -- other than for one's own internal satisfaction -- a woman might create a persona who is a woman passing as a man and then pull it off so successfully that it's indistinguishable from a persona intended to be a male. But not only am I not claiming I've met someone trying to do this -- I'm specifically trying to avoid making judgments about the desirability or validity of particular approaches.) Of course, this category could also include a persona who is intended to be a theatrical performer en travesti, or it could include a persona who is using particular items of male clothing for symbolic purposes or in the context of particular activities. But the unifying concept here is that the purpose (or at least one major purpose) is to depict cross-dressing in a historic context. (Consider parallels in other types of historic re-creation hobbies for the "non-masquerade" category and the present category. A woman doing American Civil War re-enactment who wishes to portray a soldier could approach it either in terms of portraying a male character or portraying a Civil War-era woman who passed as a man in order to be a soldier.)
On a parallel track, persona-driven cross-dressing may be informed by literary motifs or practices of questionable or uncertain historicity. For example, whether one considers the occasional account of women cross-dressing to participate in tournaments to be a literary trope, a scandalous canard, or a report of actual events, it can form the basis for a woman with a female SCA persona to take part in combat without considering it to "break persona".
Activity-related cross-dressing (persona = female, presentation = female, clothing = male)
The broad cultural and temporal scope of the SCA and the lack of a requirement (or, for that matter, a strong expectation) that personas will participate only in persona-appropriate activities opens up another major category of cross-dressing that is not necessarily rooted in historic motivations, or where the motivations may be specific to the activity rather than the overall presentation. The activity in question may be a physical one (where male clothing is more practical) or a cultural one (where the activity is traditionally male and is therefore associated with male clothing), or at its most basic level, the "activity" may simply be "wearing this particular item of clothing that happens to be historically male". In a non-clothing context, we can see this as parallel to Viking personas dining at Italian Renaissance banquets, or Byzantine nobles dancing Spanish pavannes, or Elizabethan folk rising from their reproduction Gokstad bed in their A-frame tent to put on bodice or doublet in the morning.
We do not, as a general practice, expect SCA members to be completely consistent in their activities or paraphernalia not only because of the scope of activities we participate in, but because of the practical issues presented by trying to maintain a full set of gear, knowledge, and skills for every era we might want to participate in. Gender can be thought of as only one more attribute (alongside such things as geography, era, class, ethnicity, etc.) for which we regularly make decisions regarding the level of consistency we choose to attempt.
We also need to consider the purely modern phenomenon of "gender-blind costuming" where the wearer honestly may not be aware of the historic gender-coding of the garments being worn (or may chose to ignore it for purposes unrelated to persona or presentation or activity) and chooses items based on personal taste or on availability.
Perhaps one of the more complex categories of cross-dressing is the one I've left for last: the use of cross-dressing for gender-related display that specifically draws on modern attitudes towards clothing, towards gender, and towards the symbolic function of cross-dressing. This category may cut across issues of person-persona-presentation and is probably the most subjective in interpretation since it focuses purely on the intent and purpose of the act in its modern context. From a historic perspective, it may be most strongly related to speculations on the use (or secondary effect) of en travesti cross-dressing for titillation.
The juxtaposition of an overt underlying female person (or persona) with male-gendered clothing may be used in heterosexual contexts (i.e., to a male observer) to signal a playful but "safe" transgression of historical (i.e., medieval) gender behavior. Often this is done with clothing that not only does not attempt to conceal the underlying femaleness but that often exaggerates it by cut or fit or by combining male and female clothing elements. Typically, the intent is not to present any actual suggestion of a male-male social interaction (in terms of persons or personas).
A similarly playful purpose can occur when the observer is female and the fictitious scenario presented is that of the observer interacting romantically with a nominally male presentation, but again where there is no implication of an underlying male persona or even an intent to have the presentation taken seriously as male, but rather to provide a theatrical context for female-female flirtation. The same scenario, of course, can also draw on the conventions of modern butch-femme culture to signal interest in, and provide a historico-theatrical context for, female-female romantic interactions.
My Experiences and Motivations Cross-Dressing in the SCA
So how do I interact with all this? To start with, I am a 21st century woman who -- in everyday life -- wears markedly female clothing relatively rarely and markedly male clothing essentially never. (That is, "markedly male" in 21st century terms, as opposed to formerly-male but now gender-unmarked styles.) Another relevant piece of background information is that I'm a lesbian. (Ok, so this should be a "duh!" for my regular readers, but you never know who may drop by to read these things.). In the SCA, my persona -- for the purposes I use one for -- is a 13th c Welsh noblewoman. I don't tend to do much in the way of persona performance in the sense of interacting "in persona" partly because I tend to be more interested in the research and reproduction side of historic re-creation but also because I'm simply not all that comfortable doing improvisational theater.
In the SCA, I'd say that I wear female and male clothing with about equal frequency. I don't tend to get asked about that at "home" (i.e., in the geographic region where I'm most active in the SCA). But once, when I was travelling (and, as it happened, was carrying a male outfit mostly because it took up less suitcase space) I was asked if I had a male persona and answered somewhat flippantly that I didn't have a persona I had a wardrobe.
It may have been flippant but it was also more true than not. I'm a costumer. And furthermore, I'm a researcher into historic clothing construction who uses costuming as a significant part of that research. Making costumes for both genders doubles the fun. And there's not much point in making something and not wearing it. It's not the only reason I wear male costumes, although it's the most obvious one.
But for me, that aspect of my SCA activities has nothing much to do with persona. When I wear the clothing of an 8th c Merovingian woman, I still have the persona of a 13th c Welsh woman. I don't have the persona of a 13th c Welsh woman pretending to be an 8th c Merovingian. When I wear the clothing of a 13th c. Norse settler of Greenland, I don't have the persona of a Welsh woman visiting in Greenland. And when I wear the clothing of a 14th c Burgundian man I don't have the persona of a woman trying to pass as a man. That's simply not how I do persona. For me, "persona" is a default focus to use for research and re-creation purposes when no other goal interposes itself. On the occasions when I attempt particular, specific, highly-consistant "impressions" it's more likely to be driven by the focus of some external project that I'm participating in. Trust me, if I wanted to do a well-realized, detailed "impression" based around my persona, I would have picked one with far more available everyday evidence than 13th century Wales!
So one of my motivations for cross-dressing falls in the "activity-related" category, where the "activity" is creating and wearing a wide variety of historic clothing styles. My goal is generally to try for a complete and consistent outfit (rather than mix-and-match eras, cultures, and genders) but I don't make any particular effort for a visually successful male presentation and I don't want or expect observers to treat my persona as male in this context.
I have also, on specific rare occasions, done "role-filling" male presentations when participating in some activity that called for a male participant. The specific example easily to hand is participating as one of the serving staff for the Perfectly Period Feast events, where a theatrical decision was made to follow historic models and have the serving done by nominally male personnel. For these events, I not only wore male clothing but used a male name (so other participants could address me as male). I didn't treat this as my basic (female) persona masquerading as a man but rather as an entirely separate "nonce persona" where both persona and presentation were intended to be male. (This was confusing to some observers who later associated the temporary male persona with the specific outfit I wore rather than with the activity of feast service.)
Another significant reason why I cross-dress on a regular basis is for a cluster of reasons related to being gay. In certain gender-relevant activities such as dancing, cross-dressing signals my preference for interacting with women (in a context where pretty much all the women I'd be interacting with are heterosexual). Thus, it's another type of role-filling purpose but on the activity level rather than the persona level.
I also enjoy historic cross-dressing as an expression of non-normative gender identity. Which, in a way, is a bit odd because I don't feel any similar interest in 21st century cross-dressing but I suspect it's because the esthetic I like (both for myself and as an observer) is a relatively androgynous "nominal" presentation where the clothing is used as a signifier rather than a masquerade. Or, to put it more simply, I like the look of "women who look like women wearing male clothing" but not the look of "women who look like men". In 21st century clothing, an unambiguously male-coded presentation would fall much farther along the scale of "looking like a man".
In part, I enjoy this aspect of cross-dressing because it invokes the long history of women using clothing to transgress gender boundaries and gives me a re-creative context to act in violation of the restrictions of historic gender roles without needing to approach pre-1600 activities in terms of 21st century feminism. And, in part, I enjoy cross-dressing because it provides me a context for wearing highly fashionable clothing that flatters my body (from the point of view of modern esthetics, admittedly) while signaling that the presentation is intended to invite female observers, not male ones.
Let me expand on that last point a little. In the last two years I've made a couple of high-fashion medieval outfits: the male late 15th century outfit I made for serving at the Perfectly Period Feast and a 14th century female "Gothic fitted gown". I get compliments for both of them and I enjoy wearing both of them from a costuming perspective. But when I wear the female gown, I get a noticeable amount of sexually charged attention from men who don't otherwise interact with me to any significant degree and that I don't particularly enjoy. Wearing fashionable male clothing makes me feel "sexy" without being (mis)understood by male observers that the presentation is intended for their enjoyment.
Now I've said that I don't cross-dress as a persona statement in the sense of creating a female persona who cross-dresses to pass as a man, but in fact I have created characters of this type when toying with the idea of developing more detailed back-stories for the various historic eras I play in. But so far, every time I started creating a back-story of this type it's taken off with a life of its own and turned into the plot for a historic romance novel. In fact, one of the reasons I first started researching cross-dressing, passing, and similar topics was to treat the motifs in a more historically grounded way for various fiction projects. (Yet another one of my endless "historic sourcebook" projects that have yet to see the light of day.) And, for me, fiction is probably a more successful place to put that particular type of creative endeavor than trying to enact it at SCA events.
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