A Short History of Crossdressing

Being something of a student of human nature, I’m also a firm believer that we haven’t changed all that much for many thousands of years. Ten thousand years ago people were just as smart and clever as we are today, the difference? It’s due primarily to our education and medical care.
Highly developed cultural norms help to keep our less desirable traits in check too. Which is where things have gotten interesting for those who prefer not to follow them. To be fair, some people have very antisocial and destructive characteristics, which require some kind of intervention to keep the population as a whole safe and secure.

During my readings, I have occasionally come across articles about crossdressing in a historical context. I’ve found it fascinating that what I started out thinking was my own kind of lonely and solitary perversion, isn’t really, and has been with us all along down through history. I think most of us start out that way, then learn that we are not alone after all. In part, through this website, we can find so many others of a similar persuasion and our stories are often remarkably similar. Fortunately, today there is so much more information, and increasing acceptance of this, though so much misunderstanding and misinformation still exists.

I’m not a betting person, but I would suppose not long after certain attire became the norm for men and women in a society, there were some who broke those conventions. Since this was often a secret obsession, records weren’t ever kept. When it was officially forbidden from those in authority, records are not very complimentary to those who got caught crossdressing. This would seem to apply to women trying to pass as men, as well as men passing as women. My focus is of course Male to Female crossdressing.

EnFemme Style

This was often done in the context of same sex attraction, and so many records do attest to this. This is still true, but many are heterosexual men who simply want to emulate the women they find so beautiful.

Perhaps one of the best-known historical examples of this is during Shakespearean times (1564-1615) when it was considered crude and vulgar for women to perform on stage, as a result, men and boys dressed up to play the female parts in the plays. This was a big shock to me when I learned about it during English class in high school, at which time I had already started dressing up in private. To dress up in public was still a shocking idea to me.

Think of the famous and tragic love story, Romeo and Juliette, was not played by a pretty young woman and a handsome young man, but two young men. I find it puts a different spin on it when you think of two men saying vows of love to each other.

Now I can’t help but wonder how those male actors felt about it. Certainly, some must have enjoyed playing the role, and if one was a youth at the time, perhaps it would have had a lasting effect on him, and he would always have a fondness for women’s clothes, as so many of us have a fondness for today.

Perhaps there was a group of actors who specialized in performing dressed as women, but of course this wasn’t a secret as everyone knew the females on the stage were males in disguise, which was part of the joke, as the audience was in on it too. For anyone who has studied Shakespeare, you know it can be quiet bawdy, and as an English teacher I had once said to me, if everyone got all the jokes in his plays, they might be banned. At the time entertainment was much more limited than it is now, so a play was written to appeal to a wide audience, and then as now, sexuality sells.

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Then there was what could be described as a backlash against such behavior whilst the Puritans held sway. Once again, not likely a good time to be caught in the wrong clothes!

At times, France was open about crossdressing as well. During the reign of the influential French King Louis XIV (1683 – 1715), crossdressers were expected to be part of a fancy ball. For a time, the ball wasn’t considered complete without them!

This differs from a couple of hundred years earlier when a judge condemned Joan of Arc to death because she wore men’s clothes, and was therefore able to convict her of the capital crime of heresy. There are some facts, and sometimes conflicting ones concerning a historical figure so far in the past, though this would seem to be the crux of it. Really, they just wanted to be rid of a troublesome teenager, and that was a good excuse. Needless to say, that certainly wasn’t the time or place to be a crossdresser!

Germany was in shambles at the end of WWI and a new republic came to be out of the ashes of that devastating war. As things stabilized, life started to return to normal and as new money came into the country the freedom to live your life soon began to reign. Not surprising after such a terrible war, people simply wanted peace and to be able to be themselves again, not at all unlike the boom times after WWII, during which many of us were born.

En Femme Style

There was a large gay subculture with large parties and dances attended by cross-dressed men. Sometimes they were with same sex partners, sometimes they brought wives and girlfriends. This also became a tourist draw, very similar to modern times where certain areas of the world are noted for their sex tourist trade, as was Berlin during this time. Some attended to participate, others came as voyeurs to revel in the apparent shocking behavior. Though the morality police were also there to make sure a certain degree of decorum was maintained.

Then as now, men who dressed as women were usually thought to be gay, or homosexual as it was more often referred to at the time. However, a Dr. Hirschfeld believed that many were heterosexual men who were drawn to dress in feminine attire, or those who suffered from what we now sometimes refer to as Gender Dysphoria. In 1919 he opened a clinic called the Institute of Sexual Science to study and ultimately help those persons who felt trapped in the wrong body, as well as homosexual men, lesbians and intersex people. The mandate was wide, help for those that needed it, public education, research, a museum, in addition, he also helped to educate the police so they were able to change their practices against folks despite there being no laws against crossdressing at the time. They even performed the first known sex change on a young man, who always felt as if he should have been in a female body.

Unfortunately. these good times were destined not to last, as the politics in Germany changed after the Global Crash of 1929 and Germany became much righter wing. The Jewish population became a target of officially sanctioned hatred.

So, in countries throughout the world, there are records of people crossdressing from ancient times on, even in mythology. Which I will delve into in another article.


Thanks for taking time to read my article regarding a little information about the history of crossdressing from different parts of our globe.

Here are a few questions I would like for you to offer up and answer to one or more of them.

  1. What parts of the United States do you think the general population would be more accepting of crossdressers in public?
  2. Do you live in a more conservative part of America which has not become more accepting of crossdressers or do you live in a more liberal part of America which has become or has always been more accepting of crossdressing?
  3. Have you been out in the area where you currently lived while cross-dressed and how did that first night out en femme go for you? Did you feel accepted or was the feeling much more awkward and you felt completely out of place or unaccepted by your own local population?

Thanks again for reading my article and I look forward to responses to the article or one or more of the questions I’ve posed to you above!

Sincerely, Amy





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Amy Myers

I'm 60+, hetro, married, and love dressing up! I keep saying and feeling like I'm new to this, but I have dressed from time to time since my pre teens, but just late 2018 it seems to have become of a bigger part of me, rather than just a role I played from time to time. I'm interested in music, cars, photography, and plus other interests.

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Jenny Thigh High
Active Member
3 years ago

Good read. Plus the thought of Romeo and Juliet played by a young man and CD.

Whew….HOT!!!!! 😉 That’s a play I would see again and again and again 🙂

Marie Chandler
Trusted Member
3 years ago

Thank you for writing this piece, Amy. I’m endlessly fascinated with CD history. I’d love to see more articles like this on CDH.

3 years ago

Hi Amy, Nice article. You touched on Joan of Arc. There were many other women who dressed as men, simply because women were excluded from science, business and so on. These brave and intelligent women, often with help from sympathetic men, would adopt the attire and mannerisms of men to get into lectures, learned societies and so on. Some joined the military and went to war. How glad I am that as a society we have moved on so that (in most societies) it makes no difference what your gender is to study and work (and yes, I am aware… Read more »

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