Famous Crossdressers in History

Every story has a beginning, and crossdressing isn’t an exception. Although the idea seems to be gathering momentum in recent days, it has been around for centuries. Who are some of the famous crossdressers in history? What made them famous?

The famous transvestite in history disguised themselves to excel in different industries.

For men, some dressed for fun, imitation, and as a source of livelihood.

Looking at history, some people crossdressed so that they could be monks, rule empires or pose a threat to their seniors, e.g. (Francois, De Choisy, Writer 1644- 1724).

The pressure to marry and produce is another reason why some figures became famous.

So, who are the pioneers of female impersonators?

We are going to look at some of the famous crossdressers.

How did they feel about crossdressing?

We will also look at the impact they have on society.

1. Who are some of the famous Crossdressers in history, and what did they do?

Famous crossdressers in history include some of the most iconic and influential figures throughout time.

While their reasons for donning clothing typically associated with the opposite sex vary, one common thread between them is how good it makes them feel.

Elagabalus, Emperor 

At the age of 14, Elagabus became the Emperor of Rome.

He depleted his whole body and wore makeup.

He made a monetary offer to doctors who could do surgery and make him a woman.

None of the acts made him accepted.

He married the priestess who had been sworn to virginity.

He instituted the sun-worshipping religious practice that was disputable. They eliminated him at the age of 18 years.

Tim Curry

A British actor, Tim Curry is best known for his roles in “The Rocky Horror Picture Show” and “Clue.”

He has also crossdressed on occasion, both on stage and screen.

Francois De Choisy, Writer 

He was a French author. His mother dressed him in girls’ garments until he was 18 years old.

The reason for her crossdressing was political. He was dressed like that to stop posing a threat to his older brother, King Louis XIV.

Charles D’Eon, Diplomat 

He was a French spy diplomat deployed to Russia to reestablish diplomatic relations between countries.

He managed to become a maid of honor to the Russian Empress.

At some point, there was speculation about whether he was a male or female.

He demanded recognition as a woman. He claimed he had been born female and raised as a boy because of an inheritance dispute.

Fred Astaire 

An American dancer and actor, Fred Astaire is best known for his work in Hollywood musical films.

He occasionally crossdressed in his movies, most notably in the 1935 film “Top Hat.”

RuPaul 

An American drag queen, model, author, and television personality, RuPaul is one of the most famous crossdressers today.

He has appeared on numerous TV shows and films and has even released his cosmetics line.

2. How did these individuals feel about    Crossdressing in the opposite gender’s clothing, and why did they do it?

Odd enough, the answer is in the question itself.

There are several reasons why these individuals crossdressed. 

Famous crossdressers in history include some of the most iconic and influential figures.

While their reasons for donning clothing typically associated with the opposite sex vary, one common thread is how good it made them feel.

Similarly, legendary Chinese general Cao Cao also crossdressed on occasion.

While it’s unclear why he did so, it is speculated that he felt it gave him an edge in battle.

Whatever the reason, it’s clear that Cao Cao found strength and power in his feminine side.

Confidence 

Most of these crossdressers admit to having felt more confident.

This is because they could express themselves in ways that felt true to their inner selves.

Whether it was for battle or simply because they felt more comfortable in women’s clothing, these men all found confidence when they let their feminine sides shine through.

More Powerful 

In addition to feeling more confident, many crossdressers also felt more powerful.

This is likely because they were bucking societal norms and expressing themselves in ways that were considered taboo.

By stepping outside of the box and embracing their femininity, these men found a sense of power and control that they may not have otherwise had access to.

Special 

Finally, many of these crossdressers felt special.

This is likely because they were doing something considered unusual or even dangerous.

By embracing their femininity and defying societal norms, these men found a sense of uniqueness and specialness that was likely empowering.

3. Why did they do it?

There are various reasons why characters dressed in women’s clothing in history.

For religious reasons

History and mythology are full of crossdressing incidents.

In most cases, men used to dress like women or act like women for religious worship in different sects. 

Sexual excitement

Some crossdressers are disguised because of their desire for the opposite gender.

They did so because of their affinity to a culture of like-minded women.

They also wished to explore and even challenge the construction of gender.

Hide Identity

Figures like Bonnie Prince Charlie dressed in women’s clothing (maidservant outfits) to escape capture.

Not only him but others who also clad as women to avoid detection.

There were several male thieves dressed like women.

Plays

In the past, in many plays, men were to dress in women’s clothing before they could go on stage.

An example is Oscar Wilde’s ‘The Importance of Being Earnest.

Many of the impersonator parts made many men make a career of playing them. 

4. What impact did their crossdressing have on society and their respective fields of work and study?

We can make a better world for crossdressers.

We can make way for crossdressing to be more accepted in our society.

If you are comfortable with your gender and identity, express it in any way you want.

The early crossdressers left a mark on society and their respective fields of work and study in several ways.

It enabled society to accept that crossdressing is not only about sexual arousal, but there are several reasons attached to it.

It demonstrated that not all men are perverted fetish.

It brought freedom when more and more people came out as crossdressers.

Though some are still in the closet, the majority have been able to come out.

It helped men and society to see that it’s okay to be feminine.

It is not a must for every man to be muscular.

You can embrace your feminine side and improve your overall well-being.

The big margin of the fear of being outed is slowly fading.

The majority now never worry about being crossdressers. 

It has brought gender balance where some duties that were perceived to be for men are now shared equally.

Men have been accepted in women’s fields so have women in men’s fields.

Crossdressers can meet with fellow crossdressers.

Even organizations and clubs where they meet, mingle then discuss issues affecting them.

This is something that hasn’t been there.

Society, families, and professionals can better understand and make the right decisions regarding gender, sex, and crossdressing.

5. Lessons from these historical figures about gender identity and expression in today’s world?

Crossdressing has been there for centuries, but you can mistake it for a modern phenomenon.

You have learned that historical figures could dress in women’s clothing for various reasons.

Another fact you can learn is that crossdressing is more accepted nowadays than before.

You can now walk freely or identify yourself as a crossdresser without fear.

Initially, you could hide your gender by crossdressing.

Nowadays, the world can accept you as you would like to be recognized. 

It is possible to change the norms and customs of your culture because today’s world has accepted the gender identity of different persons. 

Historically, crossdressing was associated with and engaged for various reasons.

In recent years, it has been culturally associated with homosexuals and lesbians.

Men crossdressed to access spaces meant for females only.

Some wanted to illustrate their proposition. Most of them came from upper-classmen.

The 19th century marked the beginning of modern homosexuality.

The act of men crossdressing as women was to attract males for sexual encounters.

In today’s world, you can express your gender identity in whatever way makes you feel good.

You don’t have to fit in. whoever makes you feel comfortable.

Again, it can be hard to navigate the world of crossdressing because gender identity is a personal issue.

Nowadays, the better part is that you can reveal your gender identity to those close to you, not like in history, where you had to hide your identity until death. 

There is a need for you to be who you are.

Let others who are like you to come out.

It is through such ways that you will get respected.

You will enlighten others on the subject.

If you are comfortable doing it in the closet, that is fine. If you are okay to go public, the better.

Today’s world is more accommodative, and you are free to mingle with fellow crossdressers. 

Crossdressing has come a long way.

There are several hurdles that, as a transvestite you will encounter.

Judgment, societal norms and culture, and discrimination.

Nonetheless, the phenomenon in the history of crossdressing is not a big deal anymore. 

The experience of crossdressing differs from one person to another.

The way you feel is different from the other.

Just do what you think makes you comfortable.

With that in mind, look within yourself and see what you need.

You have got this. Good luck in expressing and finding yourself!