Expressing and presenting gender is a complex practice. Centuries of social and political shifts have changed our cultural understanding of gender so many times, it feels impossible to begin to unpack it all. One of the most substantial examples of intentional gender presentation is the practice of cross-dressing. The term cross-dressing is broad and has diverse meanings. The act of crossing gender boundaries through clothing is and has been employed by many different groups of people throughout history, for a variety of reasons (Suthrell 115).

My interest centres on the role cross-dressing has played in the lives of women, as both an explicitly criminal act and a subversive countercultural practice. From breeches to Bond Girls, from escape to performance, cross-dressing has played a significant role in women’s sartorial histories of resistance and advancement.

The ‘Bond Girl’

When thinking about women cross-dressing, spies and disguise come to mind. The ‘Bond Girls’ of the James Bond films are unsuspecting examples of this. One such example is the prominent inclusion of trousers in many professional and activewear costumes, which spoke to the athleticism and physical strength, more ‘masculine’ traits, of the ‘Bond Girls,’ (Germanà 115). Since Ian Fleming published the original James Bond novels from 1953-1966, and the first film, Dr. No, was released in 1962, Germanà notes that “the time frame of [the original] novels and the earlier films” contextualize the significance of the women wearing trousers and other “masculine clothing” (113). This version of cross-dressing wasn’t meant to express a different gender identity, but rather to incorporate “physical fitness, dynamic action, and professional rigour” to the ‘Bond Girls’’ existing femininity (Germanà 113).

The costumes of the ‘Bond Girls’, and indeed other women in James Bond films, like Judi Dench’s M, appropriate masculine styles in professional and action wear (Germanà 125). These costumes sartorially communicate a “dynamic picture of a clash between Bond’s vulnerable masculinity and the Girl’s hard femininity” (Germanà 125).  

The Escapee

Going beyond fiction, cross-dressing as disguise was key in the courageous attempts of African Americans to escape enslavement. This practice was particularly complex, as forced cross-dressing was used as a tool of punishment and humiliation (Bradley Foster 49). Although fewer women attempted to escape, often due to the connection between age and childbearing, they also were more likely than men to resort to cross-dressing if they did make the attempt, as traveling independently and covertly as a man was far safer than as a woman (Bradley Foster 50). Famously, Harriet Tubman wore men’s clothing during many of her journeys assisting the escape of others (Bradley Foster 50). Here, cross-dressing was not only reclaimed as a tool of survival, but also demonstrates the complex intersectionality of gender and race.

The Social Threat  

Women cross-dressing was—and at times still is— considered dangerous unless presented in specific circumstances, because it has the capacity to threaten the destabilization of a patriarchal social order (Sears 65). For example, in nineteenth-century San Francisco, anti-cross-dressing laws were enforced against women who wore men’s clothing in pursuit of “economic independence, political voice, sexual autonomy, and free movement through public space” (Sears 63). Women would dress in men’s clothing to go to bars, travel in unsafe parts of town, and protest for dress reform (Sears 64).

Notably, the criminalization of cross-dressing was not necessarily about the act itself, as this legislation only applied to public cross-dressing, but rather represented an attempt to control and squash perceived “social threats” (Sears 65).  Women who were arrested for cross-dressing were inconsistently charged, and were often let off without sentencing or further legal consequences if they were wealthy and white (Sears 65).

The above video provides a brief overview of the origin of cross-dressing laws, and provides necessary contextualization of ways in which dress has been policed throughout history and culture. From policing women’s dress in Ancient Greece, to Catholic sumptuary laws in Renaissance Europe, to Quebec’s 2019 ban on religious symbols (which disproportionately impacts veiled women) the video demonstrates that the system of legislating dress practice has long been (and continues to be) a strategy of social and political control.

The ‘Male Impersonator’

In a theatrical context, women cross-dressed in public as early as the mid-1600s in England (Geczy and Karaminas 114). Clothing was the primary way to convey a different gender presentation, so much so that the roles women could occupy in Shakespearean plays, vaudeville, and operas were known as “breeches roles” (Geczy and Karaminas 114). Simply by wearing men’s clothing, specifically breeches, female actresses would be accepted as male characters largely without question (Geczy and Karaminas 114).

Performers who cross-dressed in this capacity throughout history are known as ‘male impersonators’ rather than drag performers, because they “attempt to produce a plausible performance of maleness as the whole of [their] act” (Geczy and Karaminas 115). This is in strong contrast to the performance of drag, as drag typically relies on the audience’s knowledge that the performer is not the gender they are performing as.

Male impersonators were also popular in British music halls, such as Vesta Tilley, who famously performed the role of Burlington Bertie.

The Drag King

While drag queens (often gay men who “[mimic] and [exaggerate] ideal characteristics or stereotypes of women”) are more mainstream in the world of drag—due to a lengthy and complex queer history and recent commodification of drag through popular media like RuPaul’s Drag Race—this article is focused on the far less visible and celebrated drag kings (Geczy and Karaminas 111). Drag kings are typically women who perform drag, a version of cross-dressing that is distinctly different from a ‘male impersonator’ as discussed above, who perform a “[theatrical] masculinity” that incorporates “impersonation, understatement, hyperbole, and layering” (Geczy and Karaminas 111).

Some feminist critique of drag is tangled in transphobia, as there is a “tradition of feminist skepticism around the inclusion of transsexual women in feminist politics” and a recurring accusation against drag kings of “valorizing hegemonic masculinity, reinforcing patriarchal norms, or engaging in the subjugation of femininity through performances that use masculine tropes” (Basiliere, 979).

Many scholars reject this reading of drag, and instead understand it more as an “articulation of queer identity through cross-dressing” or subversive, counterculture engagement with gender (Geczy and Karaminas 111). Judith Butler suggests that the study of drag is compelling “because of the mundane that drag encapsulates,” and, citing Halberstam’s “claim that drag kings detach masculinity from maleness,” Basiliere notes that drag king performances “actually undermine versions of masculinity that denigrate or exploit femininity” (989, 991).

In the above video, drag king Isabel Aman notes that performing has a drag king has helped to develop her confidence and gender identity. This anecdotally supports Basiliere’s assertion that drag kinging is a performance of feminist masculinity that “diminishes the pressures of a bi-gender society” (999). On the issue of the disproportionate popularity of drag queens and drag kings, Amran notes that “it has to do with who has historically dominated queer spaces” and how “people see femininity as performative more naturally than they do masculinity.”

Always Other

Regardless of the context, whether the practice represents the advancement of women’s rights, the destabilization of social and political gender norms, a tool of survival and escape, an expression of queer identity, or a theatrical performance, women who cross-dress are criminalized, othered, devalued, and otherwise misunderstood. Cross-dressing was at times considered criminal, even deviant, but has always marked the practitioner as a counter-culturalist on some level or another. The very act of cross-dressing suggests a transgression of a dichotomous boundary—one that is at once personal and systemic. Women, historically, have been confined by rigid boundaries; boundaries that are further complicated by race, class, and other intersecting identities. It is my belief, then, that cross-dressing in any and all forms is inherently radical and demonstrates just how powerful dress can be.

Creative Component

In support of this project, I created a photo book on Canva to provide a visual understanding of what women cross-dressing looked (and look) like in different contexts. This was a more challenging endeavour than I initially thought it would be, as there is sparse visual documentation of historical cross-dressing, and even less of women cross-dressing specifically.

Additionally, the representation of white women greatly exceeded that of any other race. Even when searching for modern drag images, there are far far more images of drag queens than kings, and nearly all the sources that do feature drag kings are about how pervasively invisible many drag kings and male impersonators are and have long been.

Future work on this project would require careful searching of archives, and likely a broadening of search terms beyond just ‘cross-dressing’ ‘drag’ and ‘male impersonation’ to account for a greater range of cultural and political contexts.

Works Cited

Basiliere, Jae. “Staging Dissents: Drag Kings, Resistance, and Feminist Masculinities.” Signs: Journal of Women in Culture and Society, vol. 44, no. 4, 2019, pp. 979-1001.

Geczy, Adam, and Vicki Karaminas. “Drag: Of Kings and Queens.” Queer Style. London: Bloomsbury Education, 2013. 111–122. Subcultural Style. Bloomsbury Fashion Central. Web. 21 Apr. 2021. <http://dx.doi.org.ezproxy.lib.ryerson.ca/10.5040/9781350050723.ch-005>. 

Germanà, Monica. “‘Cross-Dressing’: From the Field to the Boardroom.” Bond Girls: Body, Fashion and Gender. London: Bloomsbury Visual Arts, 2020. 113–154. Bloomsbury Fashion Central. Web. 21 Apr. 2021. <http://dx.doi.org.ezproxy.lib.ryerson.ca/10.5040/9781474204057.ch-003>.

Foster, Helen Bradley. “African American Enslavement and Escaping in Disguise.” Dress Sense: Emotional and Sensory Experiences of the Body and Clothes. Ed. Donald Clay Johnson and Helen Bradley Foster. Oxford: Berg, 2007. 47–59. Bloomsbury Fashion Central. Web. 21 Apr. 2021. <http://dx.doi.org.ezproxy.lib.ryerson.ca/10.2752/9781847887139/DRSENS0010>.

Sears, Clare. “Problem Bodies, Public Space.” Arresting Dress: Cross-Dressing, Law, and Fascination in Nineteenth-Century San Francisco, Duke University Press, 2015, pp. 61–77.

Suthrell, Charlotte. “Crossing Gender Boundaries in Cultural Context: Fieldwork Comparisons and Cultural Influences.” Unzipping Gender: Sex, Cross-Dressing and Culture. Oxford: Berg, 2004. 115–130. Bloomsbury Fashion Central. Web. 30 Apr. 2021. <http://dx.doi.org.ezproxy.lib.ryerson.ca/10.2752/9781847888952/UNZIPGEND0008>.