Cross dressing: definition, history and origin

Clothing and its association with the "opposite" gender

As a term, cross dressing can conjure up confusion. How do we define what cross dressing is and the practice of cross dressing? Is it determinative of gender identity, sexual orientation or entirely unrelated? At the core of the matter, all of this gray area is the entire point. Cross dressing reveals, through its embodiment, the ever-changing space of gender and identity. 

This blog will set out to answer a deceptively not so simple question: what do we mean when we talk about cross dressing?

What is cross dressing?

Cross dressing is the practice of wearing clothing for example dresses & heels, or suits & ties that corresponds to the binary gender identity you were not assigned at birth.

This means that, if you were born biologically male and assigned as such, wearing "women's" clothing is cross dressing. If you were born biologically female and assigned female at birth, then wearing "men's" clothing makes you a crossdresser. The quotations are intentional, as it is societal norms that label clothing as either men’s or women’s clothing.

A gorgeous crossdresser

This may seem overly basic, but in a space where terms are constantly shifting with context and evolving in their definitions, establishing the essential definition is a must.

Cross dressing as a practice is by itself not defined or bound to gender or sexual orientation parameters.. Crossdressers can be homosexual or heterosexual. They can be transgender, or not. It can be related to a sexual fetish, or completely unrelated to sexual pleasure. The definition of cross dressing is simply that - wearing clothing or articles of clothing that society has determined is the opposite of what sex you were assigned with at birth. In western society or culture, the term crossdresser is usually associated with a cis-gendered heterosexual male who wears feminine clothing and accessories.

Oftentimes, crossdressers receive societal backlash as they are resisting societal norms - but it’s important to know that crossdressing isn’t considered pathological or associated with a particular disorder. Crossdressers may cross dress their entire lives or for a certain period of time only.

A brief history of cross dressing

One of the misleading misconceptions of cross dressing assumes that this practice is somehow new, postmodern, a symptom of societal malaise or confusion in the contemporary era.

Not only is this idea patently wrong, but it couldn't be further from the truth.

Dressing as the opposite sex (or, more broadly, in a way specifically outside of your assigned gender role), has been around for longer than history has been recorded.

A beautiful crossdresser

Gender, mythology, and society

Dressing to re-organize gender identity appears in all cultures. Asian and Native American cultures have specific cross dressing cultural aspects - Hindu mythology has stories that concern the transcendence of the gender binary. Certain cultures and languages even define a third gender, one that in a sense both combines and reveals as an illusion the distinctions between man and woman.

A pair of Hindu crossdressers

For some, cross dressing has a defined sacred or ritualistic function. For others, cross dressing served practical purposes, such as subverting male power dynamics, performing on stage  or, of course, self-expression.

For much of the western theatrical tradition up to the 17th century, women were forbidden from acting in plays. Male actors cross dressed to play women characters from the ancient Greeks through Shakespeare and beyond.

Gender barriers, crossdressing and women

One common cause for cross dressing, most often practiced by women, is to bypass gendered barriers.

A painting of Joan of Arc

We see examples of this in Joan of Arc, the soldier and Christian martyr who wore the clothing of a soldier, and Hatshepsut, the second female pharaoh of ancient Egypt whose statues often bear a ceremonial beard and traditional kilts of a king.The distinction between "Eastern" and "Western" civilizations is dubious, to say the least, but the generalization can be made that those known as western societies have historically carried strict rules forbidding women from wearing male clothes.

Much of this stems from Judeo-Christian holy text and modesty traditions, but has been reinterpreted to suit the aims of one regime or another. Women pioneers have always been breaking the rules, however, and certain crossdressers were famous, in their own day and historically, for "passing" convincingly.

Crossdressing and men: Charles d'Eon

Perhaps the most influential male crossdresser of the 18th Century was a French nobleman, diplomat, soldier, and spy named Charles; usually called the Chevalier d'Eon. Recruited into a secret ring of spies by King Louis XV, Charles was an important agent of the French court for decades.

A painting of Charles d'Eon by Thomas Stewart

He also went by Charlotte: he cross dressed so convincingly that he did a great deal of important espionage as a woman. From the age of 49 until his death at 81 (in 1810), he lived almost entirely as Charlotte.

The Chevalier is a good example of what used to be called "dual-role transvestism." This clinical and outdated term described an individual who maintained a life presenting as their birth-assigned gender and a separate life presenting as the opposite gender.

We may recognize it as a description of what many people do today: maintain two personas, one that wears "male clothing," and another that wears "female clothing." These personas can overlap, and be nearly indistinguishable from one another. Or they can be almost entirely separate, lived as distinct lives inhabited by one individual.

The scare quotes here are meant to illustrate that the labels male and female are profoundly arbitrary. Clothing is costume, whether bold or demure, and crossdressing allows the freedom to play with these received notions of "correct" dress.

Cross dressing Latin origins

To speak of terms, one has to address the word "transvestite." This word has accumulated a deeply negative connotation due to repressive pseudo-scientific diagnoses using the term, dispatched by psychiatrists who saw all male crossdressing as a negative condition. However, the etymology of the word reveals a useful definition.

In Latin, the combination of trans "across, beyond," and vestire "to dress, to clothe," produces the word - literally, to dress across or beyond the imagined line dividing man from woman. Considered this way, cross dressing is a fundamentally radical and profound act.

What triggers cross dressing?

There appears to be no universal answer to this question. Certainly, there are some common reasons given: a desire to subvert gender roles, the pursuit of sexual arousal, experimentation, to relax or reduce anxiety or simply the fascination with being something one almost is but, because of an invisible line drawn by social convention, is not. Cross dressing behavior typically begins when the person is quite young before any definite reasons govern their actions.

Is crossdressing a gender identity?

Without the larger context of an individual's overall identity, cross dressing cannot be said to be a gender identity in and of itself. While cross dressing can play an important role in one's journey toward the discovery of a gender identity that resonates with them or feels more correct than the one assigned at birth, a crossdresser is not necessarily less a man nor more a woman (in the case of male crossdressers).

A crossdresser looking in the mirror

Simultaneously, crossdressing may be a centerpiece or beginning journey of an individual's transition from one gender to another (or outside of the gender binary altogether). Eventually, cross dressing may even evolve into, simply, dressing - the style once considered other can become more natural than the gendered garb one was expected to conform to since birth. Many crossdressers consider themselves as part of a broader transgender spectrum.

Cross dressing is an act that plays amongst the stereotypes of gender in our societies and possesses the power to transcend these limitations entirely. It can be part of something larger or done for the act alone. Its root is in self-exploration, and its applications are innumerable.

Are crossdressers drag queens?

In the literal sense a drag queen is cross dressing as a woman when they are on stage, but drag queens are people who cross dress for entertainment. Drag queens also dress as caricatures of women, for comedic purposes and to play a character.  People who identify as crossdressers, however, do not typically identify as drag queens. 

How common is cross dressing?

The book "Tell Me What You Want" by Justin Lehmiller contains a survey that found roughly one-fourth of all men and women have fantasized about cross dressing. From this, we can say that the impulse to crossdress is very common, though it's unclear how many of us actually act on that desire.

As long as the social stigma remains, we won't know for sure how many of us cross dress, publicly or privately. What is indisputable is that cross dressing is widely practiced, has a long and storied history and is a vibrant current of curiosity that creates freedom and meaning in the lives of many. 

If you're an experienced crossdresser or just starting out on a cross dressing journey, En Femme is here to help you express your feminine self and has an extensive collection to fit your every wardrobe need.


  • Elizabeth Ann Osmond

    Thank you EF for all that you do and what you’ve become. As beloved author Tillie Olson so perfectly put it, for responding to “what caring asks of doing” an undertaking that cannot help but reveal us to be a part of the universe rather that apart from it, and profoundly change our lives forever. For me, crossdressing has opened head, heart and senses to new levels of awareness and understanding that allows me to navigate the world around me with a compassionate acceptance of the people and chaos that abound, and find myself not up my head, but in the magnificent and neverending efforts of others to effectively address whatever circumstance throws their way, and my unorthodox life is played out before them, it is hoped, in such accessible human terms that they, too, may see themselves in me and find it useful.

  • Rolffe

    Riktigt underbart skrivit och man känner igen sig i texten hur man kan uppnå en skön och tillfredställande upplevelse!

  • Alexis

    I am a male to female. " crossdresser " My femme name is Alexis , I only use it when fully dressed , I dress up to express my feminine side and I am genderfluid , I dont try to pass as a women and I dont desire to transition nor feel as if I am transgender , I just simply enjoy wearing womens clothes to express femininity , they are also very comfortable and help me to feel relaxed and reduces my anxiety and stress , I am not 100% fully out to the public although I have been out many times dressed up in various levels of dressing from painted nails and earrings to full makeup and wigs , I am mostly private with the exception of a handful of friends that have accepted my feminine side.
    I am slowly getting used to going out in public and not being afraid or ashamed to be myself , its a work in progress. I dont really accept the term crossdresser I prefer my personal label as feminine expression , or being a feminine expressive male or F.E.M. I came up with that term myself with an online friend.

  • Jane Weston

    My origin began between the age of 4 or mother let me play in her nylon stockings. At age 8 my aunt saw me pulling on some stockings and admiring myself. That was the first of many “it is wrong for little boys to wear women’s things”. That was several decades ago. My aunt was wrong, "it is wonderful to enjoy and wear women’s things!… " Please embrace, enjoy and have fun Dressing. Jane Weston

  • Stevie

    I crossdress, i more than a crossdresser! I m a heterosexual non trans make that crossdresses
    I love all
    I accept all
    I love to mix the clothing of both genders
    Panties bras womens jeans
    Toe nails painted
    Shaved chest cute landing strip
    Underarms shaved
    I m me !

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