Crossdressing: Have Your Cake and Eat it Too

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...give a little scenario

This article seeks to further investigate the phenomenon of crossdressing in its most basic terms --- what it is, why people do it, and where it fits in the world of cross-gender human existence. It seeks to put crossdressing in the larger context of transgender experience.


The word "transgender" arose in the 1990's as an umbrella term for a variety of "gender-different" people, usually defined as crossdressers, transsexuals, genderqueer, etc. As an umbrella term, it has no precise definition, other than some sense of gender non-conformance. A better definition of "transgender" can be had by applying the word, not to people, but to human feeings, thoughts and experiences.

It has been said many a times that gender is a "social construct," as opposed to sex, which is "biologially determined." By this we mean that the (often) relatively simple categorization of people into male and female categories is extended to a wide range of artifacts, activities, experiences and even feelings --- the social construct.

For example, consider the conventional colors of pink for baby girls and blue for baby boys. As ingrained and "natural" as that may seem to us today, the rule was actually reversed 100 years ago --- pink for baby boys and blue for baby girls! That is why Disney's Snow White was dressed in blue, but the more modern Disney "princesses" wear pink.

In this way, a wide variety of human experiences become gender-coded. Dolls are for girls, trucks are for boys. Dancing is for girls, sports are for boys. Skirts are for girls, pants are for boys. Cooking and cleaning is for women, working outside the home is for men. There is nothing 'intrinsicly' masculine or feminine about any of these activities or artifacts.

Transgender Experience

With that in mind, the phrase "transgender experience" may be defined as 'an experience that challenges or otherwise goes against conventional gender expectations.' The word "transgender" describes something that is, in one way or another, not conforming to conventional gender expectations. Just like a 'transatlantic relationship' involves people on two sides of the ocean, a 'transgender experience' involves a person and an experience on two sides of the gender spectrum.

Although the word "transgender" sounds scary, transgender experiences are actually quite common. They might include a woman pursuing a career in rocket science, a boy who likes to dance, a woman serving as a football referee, etc. Every day, we read about men and women who don't let gendered expectations get in the way of what they want to do in life.

Since gender is a social construct, the idea of transgender also relies on that social construct. Depending on the social setting, an experience may or may not be considered transgender. For example, many people would consider any kind of dancing by a boy to be transgender; whereas those acquainted with the ballet world do not.

Case Study: Boys in Ballet

Ballet for boys is a transgender experience in America today, because that is how it is perceived by the majority. The ratio of girls to boys studying ballet in the elementry years is literally 100 to 1. In spite of the strong negative social pressure, a small number of boys persist anyway. Clearly, it is something important to them. It is interesting to note the strategies boys typically employ to manage and justify their participation in ballet to their friends.

Boys will, almost exclusively, point out aspects of ballet that are stereotypically masculine (and heterosexual). They will point out the high amounts of athleticism involved, especially for men; that the tights they wear are specially made for boys; that they get to hang around beautiful girls in skimpy outfits. Sometimes, boys will play on homophobia to portray "macho" sports as being maybe less masculine than they first appear; for example, football players wear tights and grope at each other.

The above strategies, so commonly employed, completely fail to address the trasngender aspect of ballet for boys. Ballet is an art form that objectifies and displays the human body --- something reserved for, in fact required of, women in our contemporary gender models. The average Joe on the street understands this, and can easily see through strained explanations about athleticism and pretty girls.

Boys who study ballet --- especially if they started below the age of ten --- often do so because they like making beautiful art with their bodies. If they just wanted to be athletic, they would do track and field, or football, or basketball, or karate, or one of dozens of other activities.

Thus, we have a situation in which boys who study ballet rarely give the real reasons for their interest, and almost uniformly refuse to confront our society's gender expectations. By pretending that they're really in it for the pretty girls, they can engage in something they deeply enjoy, while at the same time not having to do the hard work of confronting constricting gender sterotypes head-on; they can have their cake and eat it too.

It is the rare boy indeed who says to his peers "I study ballet because I love making beautiful and graceful movements with my body."

Transgender People?

If transgender experiences are common, the natural question is, what makes a 'person' transgender? Certainly, having a couple of transgender experiences here and there does not make one transgender. Why do some people choose to cast their transgender experience through the lens of a transgender identity, whereas others are happy to not identify personally with it? Is trangender even a coherent grouping for the purposes of identity politics?


With a model of trasngender experience, we can address the more specific issue of crossdressing. The dictionary definition is "the wearing of clothes designed for the opposite sex" ( Simple enough, and seemingly sufficient --- crossdressing is the borrowing of fashions between genders --- until one looks at crossdressing in practice. There are organizations that promote crossdressing --- or more to the point, provide a support forum for people who want to do it. The materials produced by these organizations are a good place to get a more nuanced definition of the practice.

Tri-Ess (the Society for Second Self) is one of the largest and oldest national crossdressing organizations. It is a registered nonprofit organization with 35 chapters throughout the United States. Right on the top of its website is a link to "What is crossdressing." "Crossdressers" are defined as "people who dress in clothing normally reserved for the opposite sex." This is essentially the same as the Mirriam-Webster Definition, although the word "reserved" begs the question of who makes the reservations?

If it were only that simple. Crossdressing, as practiced by Tri-Ess is not just wearing clothes that were "designed" or "reserved" for the opposite sex. Tri-Ess also talks about the understanding "woman within" and about the "second self." The Chi chapter of Tri-Ess elaborates on this: "we cultivate a complete feminine image, with undergarments, makeup, wig, padding for hips and breasts, and even a femme name" (

Additional websites provide even more information on what crossdressing is 'really' all about. Wikihow ( has an article called "How to Crossdress" giving step-by-step instructions. Step 6 reads: "Make sure to buy.. some panties somewhere, or get one from a girl. It is always fun to go get fitted at Victoria's Secret."

Wikihow links to a "related wikiHow" called "Pass as a Woman." It goes over a dozen or more details that a man must pay attention to if he wants to "look like a woman" in public; those include stubble, eyebrows, nails, wigs, makeup, padding, body-shaping underwear, "feminine" gestures, postures and voice. None of this is unique to Wikihow; it is standard fare in the crossdressing community. Some people do try harder than others to "pass" as a woman.

In any case, it is clear that crossdressing is not just about borrowing fashion, but actually about impersonating the other sex.

The Woman Within

One common explanation of crossdressing is that men who crossdress have a "woman within." Crossdressing allow them to access this "feminine side," allowing them to be more fully human. In fact, it is suggested that all people have a "masculine side" and a "feminine side," like ying and yang in different portions. Crossdressers are described as being simultaneously more in touch with these two sides than the average Joe. In going through life, the crossdresser has two modes of operation --- one male and one female --- in order to access these two sides. The process of transforming to the "en femme" mode is meticulous and highly ritualized.

In light of the transgender experience model above, the Woman Within theory requires some critical evalution. The problem with it is that it reinforces our gendered overlay on inanimate objects and experiences. Feelings and desires labelled as "feminine" are assigned to the "woman within." The crossdresser only allows himself to experience those feelings when "en femme." In this way, just as with the issue of boys studying ballet, the crossdresser is able to avoid a direct confrontation with our gender stereotypes.


Related to crossdressing as described above --- commonly called "heterosexual crossdressing" --- is the drag phenomenon. Drag is a theatrical stage act of female impersonation, often but not always within the gay community. The drag queen does not try to "pass;" no one really believes that he is a woman, any more than anyone believes a stage actor really is the person being represented. Rather, the drag queen seeks to portray an outrageous, comical image that is entertianing to watch.

Drag has a long history in theater. The Trockaderos, an all-male comedy ballet troupe, can be seen as continuing this tradition in a ballet setting.

Crossdressing as Theater

Although "regular" (non-drag) crossdressing is not a theatrical act per se, it shares much in common with theater. Like an actor preparing for a show, a crossdresser getting "dressed" goes through a meticulous routine of transformation an costuming, in order to get into a role and portray a character different from himself. Like an actor in character, a crossdresser en femme is in a different mode, a different role. The female character is separate and distinct from the "regular" actor portraying the character.

Many people find crossdressing to be strange, and rightfully so. The act of Joe padding his chest, throwing on a dress and calling himself "Suzi" for the evening can seem bizarre. Crossdressing apologists make the strained claim that this is really no different from a woman who wants to throw on jeans and a baggy sweatshirt for the day. But they fail to address what is obvious to everyone else --- that the woman in question doesn't seek to call herself "Mark" for the day, nor does she glue stubble onto her chin. If she did, we might think that is biazarre as well. Therefore, an attempt to normalize crossdressing as "simply" a form of fashion borrowing fails.

It seems that the theatrical experience of putting on and taking off roles is a better model for understanding. For the professional actor --- who tries to be versatile in the roles he or she might be able to play successfully --- gender is just one more challenge to overcome. In a sense, an actor is already "cross-dressed," no matter what gender is being portrayed. The actor at home, off stage, is the real McCoy.

Although actors usually play (gendered) people, they sometimes play ungendered objects as well --- especially in more abstract forms of theater, such as dance. It is an interesting exercise to examine our own assumptions about the gender of an actor who might portray a tree, a flower, a dog, etc.

Why do People Crossdress?

Male crossdressers almost universally claim they don't know why they crossdress, but they have to do it. The official answer is "no one knows." However, observational experience suggests that people crossdress in order to gain access to an experience they desire but could not access without crossdressing. With this theory in mind, it is instructive to look at some women who have crossdressed, all for that very reason:

  1. Joan of Arc --- crossdressed in a time in which women were not allowed to be political or military leaders.
  2. Yentl --- crossdressed in order to attend an (all-male) seminary
  3. Billy Tipton --- crossdressed in a time in which women were not allowed to be Jazz musicians
  4. Norah Vincent --- crossdressed as a reach project for her book "Self-Made Man: One Woman's Journey into Manhood and Back."

Although most crossdressing men are not so famous, the reason seems to remain the same --- crossdressing is a way to access the "woman within" who, for whatever reason, remains inaccessible without crossdressing. This begs the questions, what are these experiences that crossdressing men desire, and why is crossdressing needed to access them?

Why Not Just Wear a Skirt?

When a woman wants to feel beautiful for the evening, she might slip on a little black dress and some lipstick and go out on the town. When a man wants to feel beautiful.... well, that's a transgender feeling. Men are not 'supposed' to want to feel beautiful. But what if a man wants to experience the feeling of beauty that can only be had by wearing a little black dress and lipstick?

On option is he could wear the dress and lipstick --- just like a woman who wants to study Physics can go to MIT. However, doing so would put the man in the position of directly challenging gender sterotypes. That can be socially risky, and exposes one's feelings to the world in a way that can never be recanted. It is also perceived as inviting violence, although the experience of many men who have done just that tells a different story.

In the case that directly and publicly challenging gender stereotypes is considered too risky, crossdressing offers a way to cross gender norms while still publicly maintaining them. Women are "allowed" to wear dresses and lipstick, and to feel beautiful. If a man temporarily turns into a woman, then he can have the same experience without risking the negative consequences of breaking the rules. Like the boys who claim to like ballet just for the athleticism, crossdressing allows men to have a transgender experience without taking social risks.

The irony of crossdressing is that it absolves the crossdresser from breaking gender norms, even as he is breaking a single gender norm in a big way. Secrecy becomes necessary in order to maintain this illusion. Many people, upon finding out about the "second self," find the whole experience to be bizarre. This just adds more justification to maintain secrecy.

Interestingly, men who challenge gender norms with their choice of fashion encounter very little negative reaction. Is the "solution" of secret female impersonation worse than the "problem" of publicly challenging gender norms?

This observation has given rise to a small but growing men's fashion movement that seeks to borrow from the female wardrobe --- but ultimately seeks to repurpose the borrowed garments for itself while designing new forms specifically for men. The movement seeks to "allow" men to be beautiful and to wear beautiful clothes. We have seen this in recent years both in high fashion and on the streets.


Based on crossdressing as it's practiced by the various crossdressing communities today, it is clear that crossdressing is not just another fashion movement that involves borrowing clothes across gender lines. Rather, it is an activity in which one takes on a personna that emulates the look and mannerisms of the other sex --- or at least one's perception of the other sex. Clothing is a necessary, but far from sufficient, part of that process.

Crossdressing may be a way to engage in transgender experience without directly challenging gender stereotypes. It also bears some striking similarities to theater.

A more complete definition, therefore, might start out as: crossdressing is an activity in which one takes on a personna to emulate the look and mannerisms of the other sex. The crossdresser may or may not hope that the emulation is able to act as a disguise in public. Either way, crossdressing involves attention to some or all of the following:

  1. Clothing
  2. Alterations to apparent body shape
  3. Alterations to body, facial and head hair
  4. Behavioral alterations of voice and movement


Helen Boyd's "My Husband Betty" Other stuff... this needs to become more specific.