The Truth About Crossdressing: History, Meaning, and Misunderstandings
Crossdressing has been around for as long as people have been people. From the moment clothing became associated with gender roles, crossdressing has been an activity people have engaged in.
Generally speaking, crossdressing can be defined as wearing clothes generally associated with the opposite gender. However, a more popular understanding of the term would generally be men who wear women’s clothes. Women’s fashion has become so varied and all-encompassing that nearly any outfit doesn’t raise an eyebrow.
While often misunderstood, men who cross dress have been around for centuries upon centuries. The practice serves many purposes, and each crossdresser has their motivations for dressing. Whether for personal comfort, outward expression, gender exploration, or performance, it is a form of self-expression/exploration for the men who engage in it.
Misconceptions abound about crossdressers, and a better understanding of the background and motivations for dressing up feminine is essential to combat the all-too-common stigma surrounding it.
What is Crossdressing?
Simply put, crossdressing means wearing clothes and other accessories commonly associated with the opposite gender. For this article, we’ll be discussing male-to-female crossdressing; men who dress as women do. It doesn’t matter if the dressing is done privately or in public; if it’s done full time or only sometimes; if it’s subtle or over the top.
There are a huge number of reasons a man will cross dress; each one is personal and individual, but there are usually a few common broad strokes.
Each individual has a reason for dressing and an extent to which they engage in it. It might be an appreciation for women’s fashion and integrating some feminine style into their look. It could be an exploration of one’s gender identity, a thrilling hobby, or a relaxing escape from reality.
It’s quite important to recognize that a lot of the popularly held beliefs about men who cross dress are false. Crossdressing doesn’t automatically mean someone is gay or transgender; many crossdressers simply wish to connect with their feminine side to express a different aspect of their personality. For some, it’s a momentary escape from the daily pressures and stresses of societal expectations of masculinity.
Many crossdressers will dress up from time to time and be completely happy in their usual lives with no desire to live as a woman full time. The stigma that automatically labels men who cross dress as deviant or abnormal is damaging and not an authentic reflection of the crossdressing experience.
Crossdressing in History
Crossdressing isn’t a modern phenomenon. You can easily look back through history and find examples of crossdressing and crossdressers.
Men dressing as women has been done for performance, cultural reasons, satire, and more. By contrast, the modern concept of black-and-white lines between masculine and feminine gender roles is quite a modern and Western construct.
In many societies with differing traditional cultures, the idea of gender was more fluid, and with it, a less defined concept of gendered clothing. Even in Western societies, it isn’t difficult to find paintings of rich merchants and nobles wearing flowing robes festooned with jewelry, flaunting their wealth.
Theater and other performance art have long been venues for female characters portrayed by men. At certain times, this was because women were forbidden from acting on the stage, or other times, roles were specifically written as such. Asian cultures have a long tradition of men being cast in female roles in performance; examples can be found in Japanese, Thai, and Indian theater and cinema.
In more modern performance, there are still a host of examples going back decades of crossdressing on film and the stage. Some of Hollywood’s most famous actors in the 1950s donned dresses on film; men dressed as women have been a staple of British comedy for ages. Since the turn of the millennium, drag culture has come more to the fore, and the increased visibility of gender bending influencers on social media has largely brought it into the popular consciousness.
It’s important to recognize that a little bit of how crossdressing has been in media and performance is only the most visible way of showing that gender nonconformity has been around for ages. Crossdressers have been present in societies as well. We shouldn’t just assume that crossdressing has always been a form of performance; it’s usually a deeply personal and complicated behavior.
Common Misconceptions About Crossdressing
There are so many misunderstandings and biases about crossdressing. While it always involves some form of gender expression, many people make assumptions about an individual that will likely not be true.
The misconception is that crossdressing is all about performance and over-the-top exaggerated versions of hyper femininity, such as in drag. Most crossdressers will want to blend in and find a natural femininity that is realistic and not cartoonish. It’s just as likely that a crossdresser is responding to an inner desire rather than a need to be the center of attention.
A huge misconception is that all crossdressers are homosexual or transgender, and if they claim not to be, they are just in the closet. While it’s easy to see how these ideas would get put together, most crossdressers don’t experience the same inner struggles as transgender individuals do.
A transgender woman will want to be seen and treated as female all the time, as they should be. However, a crossdresser might only dress up occasionally or only privately and, at the same time, be completely satisfied with their daily life as their male self. Crossdressers will take huge pride and pleasure in seeing themselves transformed by clothes and makeup, but not wish to live outwardly as a female full time.
Finally, as the LGBTQ+ movement has become more and more prominent in our societies, we’ve become more aware of different gender identities and sexualities. Gender fluid or non-binary individuals will only adopt elements of feminine style to blend their outward appearance to be more androgenous and opaque. A crossdresser is probably not going halfway; just how a crossdresser will take pride in their transformation, they won’t want to go halfway. Being fully made over or dressed up on special days or at timely moments and then changing back to usual clothing is typical.
Crossdressing & Sexuality
Despite the growth of gender bending in popular culture, the common myth that crossdressers are gay remains prevalent. Oftentimes, finding out that someone is a crossdresser can doom their relationship, forever change friendships, and have massive social consequences. However, the idea that crossdressing and homosexuality are innately connected is untrue.
People from all walks of life crossdress. It doesn’t matter where on the globe, rich or poor, gay or straight, introverted or outgoing; the motivations and reasons for crossdressing are as varied as the people who do so. Automatically zeroing in on a single reason why someone dresses up in women’s clothing is narrow-minded and simple. It’s the result of outdated, bigoted beliefs and attitudes; assigning motivation based on a preconceived idea is the essence of prejudice.
A number of people will also associate crossdressing with mental instability or behavioral toxicity. No reputable psychological organization classifies crossdressing as a deviant behavior or mental illness that requires treatment.
While some people might cross dress for sexual thrills, it is not the only or even a common reason for doing so. Crossdressing is also not a destructive activity, and it doesn’t result in self-harm, violence, or addiction. It’s a personal activity that should be understood on a case-by-case basis.
The Role of Social Norms in Crossdressing
Most modern societies have strict expectations around gender and gender expression. These expectations are largely based on historical norms and cultural traditions. Over time, these norms have become measuring sticks to judge how manly or appropriately masculine a guy is. We all have grown up with these norms, and to a certain extent, we’ve all been influenced by them.
For men and clothing, these norms run surprisingly deep. Anyone who has watched popular comedy shows like “Friends” can see how many jokes are made about a character wearing female attire or accessories.
A classic storyline in a number of shows is when a male character chooses to use a handbag for their wallet and keys. There are immediately several jokes about how feminine it is for a man to carry a purse, which is inevitably explained away as being a new European trend.
While these attitudes have relaxed somewhat in the last 10 to 20 years, they persist.
Nowadays, with the advent of the metrosexual movement in the late 2000s, along with the popularity of Korean pop music and a plethora of beauty products marketed towards men, people are slightly more accepting of elements of traditionally feminine fashion in more masculine styles.
K-pop fans will tell you that some of their favorite singers wear lip gloss or eyeliner as part of their look while performing. Even some athletes have endorsed and appeared in advertising for hair or other beauty products.
However, there is still a lot of stigmas about fully dressing up to take on the full appearance of the opposite gender.
There is a lot of conjecture about why this is the case. I would argue that a lot of the hostility that crossdressers face in the world is actually a result of a threat to traditional masculinity.
After all, crossdressing isn’t a harmful or purposefully hurtful activity, and how one person dresses doesn’t affect how another chooses to dress. It’s distinctly possible that prejudice against feminine men, or men who enjoy presenting as femme from.
Fighting Stigma Around Crossdressing
Crossdressers are certainly not under any specific obligation to fight back against the negative persecutions. For those of us who choose to dress en femme privately and keep it to ourselves, there might be no utility to combatting social stigmas. On the other hand, even the smallest steps can contribute to making a big difference in the long run.
The best thing any crossdresser can do to fight social stigma is to be visible and part of a community. It’s much more difficult for people to judge and think negatively when there is community contact with people who are different.
It isn’t hard to notice that the places that are the most tolerant of diversity are diverse themselves. New York City, the birthplace of the modern LGBTQ rights movement, has always been a haven for those of us who are a bit different. Spend a day in the east village or Chelsea in Manhattan and you’ll be sure to encounter someone who is using atypical fashion for expressive purposes.
Finally, when we encounter stigma or intolerance about crossdressing, wear it as a badge of honor. Be confident, strong, and a role model.
Remember that the negative chatter is a result of ignorance and narrow-minded thinking. Rise above and be your best self.
After all, being masculine sometimes means taking risks and being daring, and there is nothing more daring than challenging yourself to be different.
Conclusion
Male-to-female crossdressing has a long and complex history. For centuries, the concept of gender and gender expression has evolved and changed. For as long as these concepts have been around, people have challenged them. Clothing shouldn’t be seen as a rigid prison for our assigned gender; it can be a tool to allow us to express ourselves how we like.
Challenging gender norms by crossdressing is a personal choice, as is how, when, and how extensive you choose to dress up. Whether it’s to relax, for a thrill, or just to try something different, embrace who you are and own it. You’ll love your feminine self just as much!
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