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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 I think this is an outdated definition because it conflates gender and sex, which we have come to understand as being different.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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  • Writer's pictureChayse

Why Can’t Men Wear Dresses?


The purpose of this research is to gain insight into the world of modern men and masculine-presenting people who are breaking traditional gender codes by wearing ‘womens’ fashion in Western Societies, especially in America. Today, men/masc people are treated as freaks if they wear what has been branded and advertised only for women. But men have been wearing dresses throughout civilization back to our most ancient ancestors. In the 19th-century, trousers came into fashion for men and have stayed popular ever since. At the same time, however, women were told they couldn’t wear pants to the point of it being outlawed. It wasn’t until the mid 20th century that it became acceptable for women to wear pants for reasons other than work or some attempt at high fashion.

Items such as clothing and accessories are not inherently gendered, neither are colors such as pink or blue. This means our societies determine what is permissible for a specific gender to wear or even act. By beginning to associate specific fashion items with a particular gender, we begin to view something as acceptable to wear, but only if you’re perceived as the correct gender. So why do we have to have this fight again? When will all clothes, colors, and accessories become universally acceptable so anyone can wear pants or a skirt and not get a second glance?


I became interested in this topic through my work as a sex worker and professional Dominatrix. The desire to dress up in women’s clothing is usually sexually driven for most clients I encounter. oHowever, some wish to wear skirts, dresses, and women’s undergarments in their day-to-day lives as well, but can’t because of the stigma associated with being a man but wanting to dress up. Another reason why I am interested in this topic because I am non-binary, and my gender expression has changed in some ways after discovering myself. As a young adult, I was hyperfeminine and wore only dresses and skirts. After coming out as non-binary, I started wearing jeans and shorts again. I save dresses for special occasions, as so many others do. I always used to wear makeup if I was going to go 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).

This topic is important to study because up until the 1960s and 1970s in America, most women’s fashion was fixated on skirts and dresses. The Women’s Rights Movement cemented the acceptance of women wearing pants. These days it is more common to find women wearing pants than dresses and skirts. Women wearing pants has very clearly not impacted their ability to be contributing members of society, so why would men wearing skirts be any different? It seems silly and a waste of time to have the reverse argument: Can men/masc people wear skirts and makeup? Wearing skirts and dresses is now usually considered dressing up.

Why are we now going through the same pushback against men wanting to dress up in skirts and dresses? If you think about society and social media – pretty people and things are worshiped, why wouldn’t people across the gender spectrum strive to be seen as beautiful? There is more focus on beauty in our media than ruggedness, for example. How do things that are stigmatized become that way? Some people hate change for the sake of just hating something. This hate is often attributed to fear of what will happen if the change is allowed. There will have to be a change in how people frequently associate softness with something feminine.

For my research, I would do a qualitative study and use interviews to collect data. There would be three categories of men/masc people that I would seek out for this study: dresses within gender norms publically, dresses outside of gender norms publically, and dresses outside of gender norms privately. The two qualifications to participate would be that they identify as a man or masculine and are over the age of 18. Seeking different perspectives will allow me to categorize their experiences and see where there is overlap and difference in their lives. For example, as previously mentioned, men who dress in skirts are usually regarded as a freak in America. By giving a voice to them, people will have the opportunity to see that maybe the man in the dress isn’t as much of a freak as people think, not that there is anything wrong with being a freak as long as no one is being harmed. For example, in my opinion, outside of work dress codes where certain items such as pants are required for safety and personal protection, people should be allowed to wear what they want.


Through my research, I hope to discover if there is a significant reason for the resistance of men and masculine people to go back to wearing dresses and skirts. I hope that I will contribute to this topic by causing people to think about how we gender items unnecessarily. More people will think about this issue and talk to their friends about it by drawing attention to it through my research. Gender expression is a hot topic right now, and there are endless opinions on what is right and what is wrong. I feel as though we are in a gender renaissance. As a result, that is causing more people to think about what their gender means to them and how they want to express it. Conversations around the topics of gender expression and gender roles will continue to happen with more frequency. As a result, we will see more people dressing and expressing themselves how they genuinely want to be seen, which is a thing of beauty.

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  • Writer's pictureChayse

“Stand up for yourself. That’s hard to do when you don’t know who you are. We’re expected to define ourselves at such an early age, and if we don’t do it fast enough, others do it for you” (Shane Koyczan, 2013).

The reality is that from as early as 18 weeks old, we are labeled by our parents, either boy or girl. Likewise, friends, families, and even strangers ask a pregnant person, ‘boy or girl?’ Then, when born, we are coded into pink for girls and blue for boys. There is no room for someone who is born intersex. Historically and to this day, intersex people get shoved into the boy or girl box based on their genitals. As children, girls get dolls, and boys get fire engines. Girls are deemed to be patient, loving, emotional, and subtly submissive to boys. Conversely, boys are allowed to be aggressive, dominant, and in charge. Girls are expected to grow up to be nurturing mothers; boys are expected to grow up and be the ruler and be the head of the household.

‘Femme,’ ‘sissy,’ ‘butch,’ ‘tomboy,’ etc., - all labels that others can proscribe us to describe our behaviors, attitudes, actions, and looks. It is acceptable to be feminine if you are perceived as a woman, but a feminine man is laughed at for his behaviors. For example, people, including other lesbians, seem to assume that all lesbians are butch or have no interest in ‘girly’ things. So if I go to the local lesbian bar as a high-femme queer dressed up for a night out, I get accused of being a straight girl that is interloping and unwelcome. Likewise, as a child, I was told to play with the girls when I occasionally wanted to play in the mud with the boys. I wasn’t welcome there either. I had been labeled as a girl and was expected to be clean and not want to roughhouse. I did not fit in my box from a young age, and now that I know I’m non-binary, I can look back and see how I expressed that at an early age.

In my work as a Dominatrix, I get to help people explore their gender expression and presentation. There is so much taboo loaded around being a man and wanting to be perceived as pretty. The taboo includes wanting to wear makeup, lingerie, and dresses. Men in some cultures used to wear high-heels, makeup, and wigs. When it fell out of vogue, some men still wore it privately, and it grew into the taboo that it is today. Men crossdressing has been the butt of jokes for a long time and is only acceptable on Halloween as a costume.

All of these accouterments that make us ‘pretty’ are perceived to be for women and weirdos only and therefore off-limits to men if they still want to be perceived as ‘manly men.’ Clothing, makeup, and accessories are inherently gender-neutral on their own; they are just things. Unfortunately, our society has created this standard/expectation that only women are allowed to be pretty and soft; oppositely, men must be rugged and hard. I do a lot of emotional labor with clients like these, affirming them that they can be pretty and soft too. Unfortunately, most go back to living as an ‘acceptable man’ after our time together. I find this tragic but speaking as someone often considered a freak of society, it can be tough to live your authentic life, so I understand why we mask ourselves the way we do.

Freak is another label that is often foisted upon us from a young age. We all are expected to look, act, and behave in a predetermined way to be accepted by society from birth. Boy or girl? In my case, even from the single-digit ages, I’ve been a little odd both in my desired gender expression and personality, so I often hung with kids that others wouldn’t. However, my oddness was usually overlooked because I also wanted to fit in back then, so I tried following the standards set to me by my parents, church, and society. As a result, I also fit in with the ‘normies’ and often was the bridge between those two worlds. When the hormones hit me at age 13, I started embracing the weird side of me with exuberance and left ‘normal’ behind me in the dust. Through music, I discovered the alternative world and never looked back. But it came with a price. I lost status in my church, my parents were unhappy, and I was cast out from hanging with the more popular crowd. Like Koyczan mentions in his talk, people say, “kids can be cruel,” but adults can be cruel to children too. Many people’s first and biggest bullies are often their own parents.

This claim that parents are often our first and worst bullies ties back into the fact that our parents are the first ones to give us a label, ‘girl or boy?’ Our immediate caregivers have hopes and expectations for us, which influences us from birth until adulthood and often past that. As we grow up, our caregivers get to know us and vice versa, and we influence each other. Should parents stop labeling their children as boys and girls and let them decide their path in life on their own? It’s hard to do because gender is so deeply programmed into all of us regardless of how we live or identify. All children should know that the world offers infinite choices and possibilities.


Koyczan, S (2013, March 8) To This Day [Video]. Youtube.

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