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  • Writer's pictureChayse

Out of the Lingerie Closet – Men Crossdressing

Introduction and Discourse

According to Oxford Languages, to crossdress is to wear clothing typical clothing of the opposite sex. I think this is an outdated definition because it conflates gender and sex, which we have come to understand as being different. The World Health Organization describes sex as biologically defined characteristics, whereas gender and gender identity are based on socially constructed features. In any society, the perception of femininity and masculinity is not necessarily dependent on female or male genitalia (Bullough, 1993). However, our gender identity begins forming when our parents learn what genitals we have and label us 'boy' or 'girl,' which can now be assessed and imposed upon us as early as 18 weeks into a typical pregnancy. Once we are born, we are socialized and raised with matching sex and gender – male or female. For example, in present Western society, the expectations are that boys wear blue, males/men wear pants, and they are aggressive; while girls wear pink, females/women wear dresses and are submissive.

Historically speaking, crossdressing was, for the most part, practiced more often by women than men because of the boost of power that comes with being perceived as a man. However, men have been recorded engaging in crossdressing as early as ancient Greece, around 700 B.C., if not earlier. Crossdressing attracts prejudice, harassment, violence, and even death. In most historical and modern societies, being a man and demonstrating masculinity has been more highly prized than being a woman and displaying femininity (Bullough, 1993). This prize on masculinity is one of many reasons why male-to-female crossdressing raises more eyebrows than female-to-male crossdressing. When modern men crossdress, we are forced to look at women's struggles with inequality, including sexual harassment, and how deeply we are ingrained to view women are less than men.

In our society, men crossdressing seems like an admission of failure of not living up to an ideal of strength and ruggedness. A man keen to slip on a dress is considered a deviant of a particularly alarming sort (Cotton, 2019). Most of the discomfort around men crossdressing is likely due to the long-learned and well-accepted but untrue notion that gender expression and sexuality are inextricably linked (jh2716, 2014). It is a myth that all male crossdressers experience a sexual component to their crossdressing. Many men wish to engage in crossdressing in their day-to-day life, and there is not a sexual fetish aspect of it (Ruskin, 2013).

Men have been wearing dresses throughout civilization, back to our most primal ancestors. Men have also historically worn makeup, wigs, and high heels. Then, in the early 19th-century, trousers came into fashion for men and have stayed popular ever since. At the same time, women were told they could not wear pants unless necessary for work. It was not until the mid-20th century with the Women's Rights Movement in America that it became acceptable for women to wear pants for reasons other than work or some attempt at high fashion. In recent years, a growing number of teenagers have been dressing to articulate or confound gender identity. This younger generation is challenging the gender norms we grew up with (Hoffman, 2009).

Among literary discussions about men crossdressing, which were hard to find, it seems that it is agreed that crossdressing has been present potentially from the moment we started assigning genders to clothing items, however long ago that was. While researching, I also found that there has always been controversy and extreme prejudice around crossdressing, regardless of the gender performing it. Most people believe that humankind has progressed in nearly all ways of acting and thinking from our time of living in caves. However, interestingly a topic like crossdressing demonstrates an issue that still instills a level of discomfort and prejudice that existed at the time of our ancestors.


I became interested in this topic through two avenues: first through my work, and then it unintentionally crossed over into my personal life. I have been a sex worker since I was 20. The majority of that time, I did primarily full-service work and dabbled in kink. Occasionally, I had clients who would bring lingerie to wear during our time together, but I did not think much of it other than I enjoyed it. I have since pivoted in my career, and now my focus is on engaging in professional BDSM work. I intentionally advertise to clients who are potentially interested in crossdressing and sissification or feminization.

The desire to dress up in women's clothing is usually sexually driven for most clients I encounter, which admittedly skews my point of view. oHowever, many also wish to wear skirts, dresses, and women's undergarments in their day-to-day lives, but cannot because of the stigma associated with being a man but wanting to dress up as a woman. Male crossdressing could hardly have a worse reputation. The concept of a man taking pleasure in putting on a pair of stockings seems laughable, pitiful – and plain sinister (Cotton, 2019). The only opportunity they have to explore their gender expression is usually with sex workers or during stolen moments at home. Gender expression can be defined as how a person acts to communicate gender within a given culture. For example, gender can be expressed through clothing/accessories, hobbies/interests, mannerisms, and communication styles. A person's gender expression may or may not be consistent with their socially prescribed gender roles (Christel, 2016).

My first in-depth exposure to male crossdressing was dating a man who secretly identified as a sissy and wanted to crossdress both during times of arousal and day-to-to encounters. He viewed himself and acted as an 'Alpha' male around others but wore lingerie beneath his appropriate male clothing and deeply feared anyone finding out. This relationship is where I came to understand the difference between crossdressing for sexual desire, as our society views it, and engaging in it to boost self-esteem or because they enjoy the aesthetics. Men who crossdress often report formative memories of enjoying dressing up.

It is hard for many to understand what could possibly be empowering or freeing to dress up as a woman. Male to female crossdressing provokes more anxiety than female to male crossdressing due to the inequality of gendered power relations (Christel, 2016). When you look at websites and internet groups of crossdressers, there is often a highly specified ideal of how a woman should look and behave. Some facets of this ideal involve a balance of the perfectly coifed submissive 1950's Housewife and the always-ready-to-fuck submissive sex kitten, which are very male-centric ideas of what it means to be a woman. When identifying the overlap of these ideals, submissiveness seems to come up the most often. Most male crossdressers are heterosexual and will submit to women only. However, their standards are wrapped up in the idea that the perfect woman is submissive. This idea originated to serve the patriarchy's agenda and is an actively harmful stereotype that women are fighting against today.

Another reason why I am interested in this topic is because I am non-binary, and my gender expression has changed in some ways after discovering this about myself a couple of years ago. As a young adult, I was hyperfeminine and wore only dresses and skirts. I did not even own a pair of pants except my work scrubs. After coming out as non-binary, I started wearing jeans and shorts again. Now I save dresses and skirts for special occasions and work, as many others do. Also, I was always raised to wear makeup if I went out of my house. These days I only put on makeup for work or an event, and it almost feels a little like putting on drag (which I still very much enjoy). Finally, I am exploring my gender expression with the love and support of my friends and family. So being able to help others on their journey is incredibly empowering.

Researching the topic of modern men crossdressing was difficult. It does not appear to be written about or studied very often. I found more studies on historical or even fictional instances of men crossdressing than academic literature from the last 25 years. Not observing the changing attitudes towards crossdressing seems like a critical mistake because we are in a gender renaissance, in my opinion. I started by searching for articles and resources through the school library system. I searched terms like 'men crossdressing' and 'crossdressing and gender expression.' I was able to find a couple of resources, and after trying various combinations of keywords, I went to Google Scholar to find articles. I ended up hitting paywall after paywall, which was frustrating, so I switched to a regular Google search and was able to find enough to get started.

It was easier to find opinions on the topic of men crossdressing than academic resources or studies. I thought that there would be more research around crossdressing than I could find. My research results on Google were skewed because of how their search algorithms work, so I did not find any articles or resources that outwardly condemned crossdressing. From my research, the articles about gender identity/expression and how it relates to crossdressing are written about now. I have been told that academic research is often a few years behind current topics, and I believe these are relatively new topics to be discussed in tandem.

Results and Discussion

During my research, I noticed several themes among the articles that appeared in searches and the pieces I selected to base this paper on. The process of doing research was frustrating because of the most common theme I found. This theme was the lack of separation of topics of crossdressing and being transgender. It was not easy to find papers that did not focus on that, especially scholarly articles. Male crossdressing is a topic that most people have an opinion on, yet it has not been studied as its own phenomenon. There is overlap between the two subjects because many transgender people begin their transition by experimenting with their gender expression through how they dress, but they are not the same. A common misconception about men crossdressing is that it means they are questioning their sexuality or gender identity (Ruskin, 2013).

Crossdressing is different from being transgender and is also not necessarily doing drag either. These three terms are sometimes used interchangeably, but they are separate things. Being transgender is when one identifies with a gender other than the one assigned at birth. Crossdressing for the sole purpose of entertainment is when it becomes a drag performance. Whereas crossdressing is dressing up as the ‘opposite gender’ (which ignores the fact that gender is a spectrum instead of a binary), usually for personal pleasure, but sometimes it is necessary for survival. The desire to “dress up” and its realization constitutes significant experiences. This realization is described as being unique and significant for their self-esteem, self-image, and perception as a “full person” (Vancato, 2013). However, as previously discussed, male crossdressing is not an acceptable practice among many societies.

Acceptance of male crossdressing was another theme that I found during my research. When officials want to discipline [someone] whose wardrobe expresses gender variance, they must consider anti-discrimination policies, mental health factors, [and] community standards (Hoffman, 2009). One topic that showed up in my research was how companies and schools are dealing with dress codes and grooming standards among the rise in the exploration of gender expression. Crossdressing is more common than many realize. It is often done in secret since it is not accepted by society (e.g., female panties worn underneath a man’s work pants, in the privacy of one’s home). Business professionals, doctors, lawyers, blue-collar or white-collar men, crossdressing does not exclude based on profession or financial status (Ruskin, 2013). Crossdressing provides an example of a norm violation (Christel, 2016). Any wholesome representation of this identity is relatively non-existent to the masses. Major feature films that feature crossdressers portray them as sexual deviants or psychopaths, or clowns (jh2716, 2014).

Most dress codes are based on gendered expectations of men and women. For example, many dress codes state that men cannot have hair past the collar of a shirt or that women have to be in high heels and wear makeup. Therefore, a man choosing to crossdress at work or school openly is usually a big deal and rarely met without pushback or approval from higher-ups and often makes the news cycle. With the explosion of access to social media over the last 15 or so years, our news cycle is now instantaneous. Unfortunately, this instantaneous access also means that there are always opinions when a story comes out about a boy or man wanting to crossdress publicly. Outward acceptance of crossdressing is limited, even among the younger generations that some news sources have said are the most experimental generation yet when it comes to exploring gender and sexuality.

A third theme that arose from my research was women’s connections to crossdressing, as historically speaking, it was more common for a woman to impersonate a man publicly. Therefore, it can be said that most of the women’s crossdressing was rooted in their desire to achieve equality. However, until the 1960s and 1970s in America, most women’s fashion was fixated on skirts and dresses. Then, the rise of the Women’s Rights Movement made it permanently acceptable for women to wear pants. Since then, more and more ‘men’s fashion has become acceptable for women to wear. Today, plenty of women openly crossdress in ‘men's clothing,’ and aside from ultra-conservative parties, there is very little focus on this. Thus, we see that the acceptability of women wearing men’s clothing has changed and the intention for doing so (Christel, 2016).

With the open acceptance of women wearing men’s clothing, I wonder why we cannot have the same acceptance of men wearing women’s clothing. For example, women wearing pants has not impacted their ability to contribute to society, be mothers, and work, so why would men wearing skirts be different? Better yet, why not remove the gendered associations with clothes, grooming, and other such things. Making these items gendered is unnecessary. Of course, there will still be the need for clothing for specific body parts being present or not, but that is easily accommodated. While the cultural belief of a binary gender system is dissolving among certain groups, people still expect others’ gender-associated characteristics to form a consistent package (Christel, 2016).

The research shows that there needs to be more research done around the topic of men crossdressing independent of transgenderism. The more it is discussed, the more normalized it will become. However, it will have to become puritanized and have any sexual component deeply removed to make it palatable for general society. Those who get sexual satisfaction from crossdressing will always be considered deviant because of our puritanical society. I think what is even more important than that is that we need to work towards removing gender from fashion. The fact that we have made it acceptable to dress like a man but not a woman reflects on our society and the value we place on being a man. This value proves that women still have not achieved equality in our society.


Bullough, B. (1993). Cross dressing, sex, and gender. Cross Dressing, Sex, and Gender | Vern L. Bullough, Bonnie Bullough.

Christel, D. A., O'Donnell, N. H., & Bradley, L. A. (2016, May 25). Coping by crossdressing: An exploration of exercise clothing for obese heterosexual women. Fashion and Textiles.

Cotton, J. (2019, February 27). The psychology OF CROSS-DRESSING -. The School of Life Articles.

Hoffman, J. (2009, November 6). Can a boy wear a skirt to school? The New York Times.

jh2716. (2014, May 7). Breaking the binds of sexuality and gender: Male to female crossdressing. Fashion & Power 2014.

Ruskin, D. K. (2013, October 18). Are all cross dressers gay? Transgender? Is it a sexual fetish? Dr. Karen Ruskin Relationship Expert Marriage and Family Therapist.

Vencato, A. P. (2013). Body, gender, sexuality and subjectivity among men who practice crossdressing. Sexuality, Culture and Politics - A South American Reader.

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