A quick Google search of “cross-dressing” reveals a glut of media almost entirely featuring men dressed as women. Even typing “women cross-dressing,” the results are riddled with men in feminine clothing. Attempting to get still more specific by searching “women cross-dressing as men,” one hardly fares better. Results typically involve either historical context, subversion of patriarchal oppression, or women in performance on stage or in film. In fact, one must search “drag king” to view subject matter exclusively on women attired as men. There is also the phenomenon of “faux-drag” in entertainment, but it is difficult in context to visually differentiate between a drag queen and a faux queen. In effect, cross-dressing is a largely one-sided field dominated by men.
It is so one-sided partly because a shift in social norms has made it perfectly acceptable for cis-women to wear clothes traditionally associated with men, with a few exceptions. Women in men’s dress has become so normalized that it’s been commodified. Women’s pants have been a norm since the ladies of the Greatest Generation suited up to cover men’s jobs in WWII. They set the precedent for their Baby Boomer granddaughters to enjoy jumpsuits, designer jeans, and pant suits. Indeed, it led to a reclaiming and de-shaming of the term “tomboy.” A girl who is “one of the guys,” while often isolated, is also elevated to a status separate from, and “better than,” girl.
Hollywood often depicts the tomboy as a girl who is less catty and superficial. She forges bonds with men easily, but female companionship is almost always lacking and the tomboy’s love life is complicated, to say the least. She is at once lauded and condemned. Her male friends see her as cooler than other girls; they feel she understands them. However, she’s either stripped of her sexuality (see: “You’re like a sister to me”) or a friend’s romantic love unrequited leaves her estranged from her peer group. The examples are plentiful: P.J. of My Boys, Monica of Love & Basketball, Jess of Bend It Like Beckham, even Anybodys of West Side Story.
These characters become icons and their styles are emulated, thus the line for what constitutes women’s fashion is further blurred. Attire like boyfriend jeans, boyfriend shirts, boy shorts, and oversized sweaters are made to shadow the masculine while maintaining femininity. This makes it ever easier for women to adopt the status tied to men’s clothing without challenging masculinity or heteronormativity. The exception to the welcoming of cis-women in men’s clothing is the large amount of backlash lesbians get when they present themselves as masculine (see: dyke, butch, bull dyke, and stud).
Conversely, cis-men who wear women’s clothing are largely chastised and ridiculed by contemporary American society. Their sexuality is brought into question; they’re assumed to be exhibiting some sort of deviance. To quote Madonna, “Girls can wear jeans and cut their hair short, wear shirts and boots because it’s O.K. to be a boy, but for a boy to look like a girl is degrading because you think that being a girl is degrading.” Truly, much of the shame and controversy associated with male cross-dressing is grounded in misogyny and sexism.
The only ways to avoid the trauma are to pass and go into hiding or obtain such status, usually through wealth or a strongly masculine physique, that said “deviance” is accepted as a quirk or a bold statement. One sees this frequently with established male celebrities. Kanye West, Jared Leto, Vin Diesel can be photographed in skirts or dresses and not lose any status because their masculinity has been proven. They also maintain enough heteronormative behavior to not challenge the status quo. Marc Jacobs and Johnny Weir, openly gay men who frequently deviate from gender norms, are given a pass because they are so exceptionally talented in their professions.
I struggle with the idea of cross-dressing because I’ve seen it used as a tool to build people up but also tear people down. It’s not the same as blackface or appropriating dress, but it can be used to the same effect. It can be used to alienate and ostracize, usually with women as targets. The cis-man in a dress making jokes at the expense of women has a lush history (see: Big Momma’s House, Sorority Boys, White Chicks, countless sketches on SNL and even All That). “Caitlyn Jenner” is already a costume, a men’s costume, and that’s deplorable. I’m vehemently against anyone using cross-dressing as a means of mocking or belittling other people.
On the other hand, a world that condemns cross-dressing outright creates another form of alienation. I don’t want a schoolgirl to be teased for a monster truck t-shirt or a boy to be bullied for choosing the rhinestone sneakers. The lines for gendered dress are blurred and they shift with time; it was once in vogue for males to wear heels of varying heights. In my lifetime alone, I’ve seen men’s jeans go from straight-legged and baggy to a skinny style nearly indiscernible from women’s jeans.
I am wont to say there should be no distinction for “cross-dressing,” that we should all wear the clothes that feel right and simply call it “dressing.” However, I recognize the power in having a term that one can claim with honor or renounce in protest. In most situations, I am of the latter camp. I can button a shirt on either side because I shop for clothing with complete disregard as to which department it comes from and damn anyone who sees fit to label me a cross-dresser because of it. Conversely, as someone who has the luxury of a generally masculine appearance, I recognize the power I have in going “full fish,” calling it and accepting it as cross-dressing, and challenging anyone who thinks any less of me because of it.
I frequent cross-dressing parties and gender bending events. In my experience, these are usually very queer spaces with people across the gender and sexuality spectra. These parties are no more good or evil than a hammer. Whether a hammer is used for construction or destruction is completely in the hands of the person who wields it. For some, it’s a testing ground to explore a side of themselves with which they’re unfamiliar. For others, it’s a chance to be their true selves or an enhanced version of themselves. Others still use these parties simply as an excuse to put on a costume.
No one I associate with uses cross-dressing parties to demean women or mock trans people. No one I know uses hammers to assault people, but that doesn’t mean the danger is nonexistent. I believe cross-dressing has the potential to normalize gender non-conformity. I know it has the power to undermine gender constructs for better or worse. It is up to us to ensure that we use it for better rather than worse.