Cross-dressing is the act of wearing items of clothing and other accoutrements commonly associated with the opposite sex within a particular society. Cross-dressing has been used for purposes of disguise, comfort, and self-discovery in modern times and throughout history.
Almost every human society throughout history has had expected norms for each gender relating to style, color, or type of clothing they are expected to wear, and likewise most societies have had a set of guidelines, views or even laws defining what type of clothing is appropriate for each gender.
The term cross-dressing refers to an action or a behavior without attributing or implying any specific causes for that behavior. It is often assumed that the connotation is directly correlated with behaviors of transgender identity or sexual, fetishist, and homosexual behavior, but the term itself does not imply any motives and is not synonymous to one's gender identity.
Cross-dressing has been practiced throughout much of recorded history and in many societies. There are many examples in Greek, Norse, and Hindu mythology. A reasonable number of historical figures are known to have cross-dressed to varying degrees and for a variety of reasons. There is a rich history of cross-dressing found in folklore, literature, theater, and music. Examples include Kabuki and Korean shamanism.
It was once considered taboo in Western society for women to wear clothing traditionally associated with men, except when done in certain circumstances such as cases of necessity (as per St. Thomas Aquinas's guidelines in Summa Theologiae II), which states: "Nevertheless this may be done sometimes without sin on account of some necessity, either in order to hide oneself from enemies, or through lack of other clothes, or for some similar motive." Cross-dressing is cited as an abomination in the Bible in the book of Deuteronomy (22:5), which states: "A woman must not wear men’s clothing, nor a man wear women’s clothing, for the Lord your God detests anyone who does this", but as Aquinas noted above this principle was interpreted to be based on context. Other people in the Middle Ages occasionally disputed its applicability; for instance, the 15th-century French poet Martin le Franc, wrote:
- Don't you see that it was forbidden
- That anyone should eat of an animal
- Unless it had a cleft foot
- And chewed its cud?
- To eat of a hare no one dared
- Neither of sow nor of piglet,
- Yet should you now be offered any,
- You would take many a morsel. 
However, women had to disguise themselves as men in order to participate in the wider world. For example, Margaret King cross-dressed in the early nineteenth century to attend medical school, as none would accept female students. While this prohibition remained in force in general throughout the Middle Ages and early modern era, this is no longer the case and Western women are often seen wearing trousers, ties, and men's hats. Nevertheless, many cultures around the world still prohibit women from wearing trousers or other traditionally male clothing.
Cross dressing in early modern Spain was prevalent among theaters and was the most popular form of entertainment. There was a fascination with female cross dressers particularly, and it was "extremely popular" in the "Golden age Comedia". Spain viewed this cross dressing phenomenon as a threat, and passed laws targeting female transvestites throughout the 1600s. Despite the negative reactions and disapproval, it continued to remain the most popular form of theatrics and a huge contribution to Spanish comedy.
There are many different kinds of cross-dressing and many different reasons why an individual might engage in cross-dressing behavior. Some people cross-dress as a matter of comfort or style, out of personal preference for clothing associated with the opposite sex. In this case, a person's cross-dressing may or may not be apparent to other people. Some people cross-dress to shock others or challenge social norms.
Gender disguise has been used by women and girls to pass as male in society and by men and boys to pass themselves off as female. Gender disguise has also been used as a plot device in storytelling and is a recurring motif in literature, theater, and film. It is a common plot device in narrative ballads. Historically, some women have cross-dressed to take up male-dominated or male-exclusive professions, such as military service. Conversely, some men have cross-dressed to escape from mandatory military service or as a disguise to assist in political or social protest, as men did in the Rebecca Riots.
Single-sex theatrical troupes often have some performers who cross-dress to play roles written for members of the opposite sex (travesti). Cross-dressing, particularly the depiction of males wearing dresses, is often used for comic effect onstage and on-screen.
Drag is a special form of performance art based on the act of cross-dressing. A drag queen is usually a male-assigned person who performs as an exaggeratedly feminine character, in heightened costuming sometimes consisting of a showy dress, high-heeled shoes, obvious make-up, and wig. A drag queen may imitate famous female film or pop-music stars. A faux queen is a female-assigned person employing the same techniques.
A drag king is a counterpart of the drag queen but usually for much different audiences, and is defined as a female-assigned person who adopts a masculine persona in performance or imitates a male film or pop-music star. Some female-assigned people undergoing gender reassignment therapy also self-identify as drag kings although this use of "drag king" would generally be considered inaccurate.
The term underdressing is used by male cross-dressers to describe wearing female undergarments under their male clothes. The famous low-budget film-maker Edward D. Wood, Jr. said he often wore women's underwear under his military uniform during World War II.
Some people who cross-dress may endeavor to project a complete impression of belonging to another gender, including mannerisms, speech patterns, and emulation of sexual characteristics. This is referred to as passing or "trying to pass" depending how successful the person is. An observer who sees through the cross-dresser's attempt to pass is said to have read or clocked them. There are videos, books, and magazines on how a man may look more like a woman.
Sometimes either member of a heterosexual couple will cross-dress in order to arouse the other. For example, the male might wear skirts or lingerie and/or the female will wear boxers or other male clothing. (See also forced feminization)
Others may choose to take a mixed approach, adopting some feminine traits and some masculine traits in their appearance. For instance, a man might wear both a dress and a beard. This is sometimes known as genderfuck. In a broader context, crossdressing may also refer to other actions undertaken to pass as a particular sex, such as packing (accentuating the male crotch bulge) or, the opposite, tucking (concealing the male crotch bulge).
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The actual determination of cross-dressing is largely socially constructed. For example, in Western society, trousers have long been adopted for usage by women, and it is no longer regarded as cross-dressing. In cultures where men have traditionally worn skirt-like garments such as the kilt or sarong, these are not seen as female clothing, and wearing them is not seen as cross-dressing for men. As societies are becoming more global in nature, both men's and women's clothing are adopting styles of dress associated with other cultures.
Cosplaying may also involve cross-dressing, for some females may wish to dress as a male, and vice versa (see Crossplay). Breast binding (for females) is not uncommon and is one of the things likely needed to cosplay a male character.
In most parts of the world it remains socially disapproved for men to wear clothes traditionally associated with women. Attempts are occasionally made, e.g. by fashion designers, to promote the acceptance of skirts as everyday wear for men. Cross-dressers have complained that society permits women to wear pants or jeans and other masculine clothing, while condemning any man who wants to wear clothing sold for women.
While creating a more feminine figure, male cross-dressers will often utilize different types and styles of breast forms, which are silicone prostheses traditionally used by women who have undergone mastectomies to recreate the visual appearance of a breast.
While most male cross-dressers utilize clothing associated with modern women, some are involved in subcultures that involve dressing as little girls or in vintage clothing. Some such men have written that they enjoy dressing as femininely as possible, so they wear frilly dresses with lace and ribbons, bridal gowns complete with veils, as well as multiple petticoats, corsets, girdles and/or garter belts with nylon stockings.
Cross-dressers may begin wearing clothing associated with the opposite sex in childhood, using the clothes of a sibling, parent, or friend. Some parents have said they allowed their children to cross-dress and, in many cases, the child stopped when they became older. The same pattern often continues into adulthood, where there may be confrontations with a spouse. Married cross-dressers experience considerable anxiety and guilt if their spouse objects to their behavior. Sometimes cross-dressers have periodically disposed of all their clothing, a practice called "purging", only to start collecting other gender's clothing again.
The historical associations of maleness with power and femaleness with submission and frivolity mean that in the present time a woman dressing in men's clothing and a man dressing in women's clothing evoke very different responses. A woman dressing in men's clothing is considered to be a more acceptable activity.
Advocacy for social change has done much to relax the constrictions of gender roles on men and women, but they are still subject to prejudice from some people. It is noticeable that as 'transgender' is becoming more socially accepted as a normal human condition, the prejudices against cross-dressing are changing quite quickly, just as the similar prejudices against homosexuals have changed rapidly in recent decades.
The reason it is so hard to have statistics for female-assigned cross-dressers is that the line where cross-dressing stops and cross-dressing begins has become blurred, whereas the same line for men is as well defined as ever. This is one of the many issues being addressed by third wave feminism as well as the modern-day masculist movement.
The general culture has very mixed views about cross-dressing. A woman who wears her husband's shirt to bed is considered attractive while a man who wears his wife's nightgown to bed may be considered transgressive. Marlene Dietrich in a tuxedo was considered very erotic; Jack Lemmon in a dress was considered ridiculous. All this may result from an overall gender role rigidity for males; that is, because of the prevalent gender dynamic throughout the world, men frequently encounter discrimination when deviating from masculine gender norms, particularly violations of heteronormativity. A man's adoption of feminine clothing is often considered a going down in the gendered social order whereas a woman's adoption of what are traditionally men's clothing (at least in the English-speaking world) has less of an impact because women have been traditionally subordinate to men, unable to affect serious change through style of dress. Thus when a male cross-dresser puts on his clothes, he transforms into the quasi-female and thereby becomes an embodiment of the conflicted gender dynamic. Following the work of Butler, gender proceeds along through ritualized performances, but in male cross-dressing it becomes a performative "breaking" of the masculine and a "subversive repetition" of the feminine.
Psychoanalysts today do not regard cross-dressing by itself as a psychological problem, unless it interferes with a person's life. "For instance," said Dr. Joseph Merlino, senior editor of Freud at 150: 21st Century Essays on a Man of Genius, "[suppose that]...I'm a cross-dresser and I don't want to keep it confined to my circle of friends, or my party circle, and I want to take that to my wife and I don't understand why she doesn't accept it, or I take it to my office and I don't understand why they don't accept it, then it's become a problem because it's interfering with my relationships and environment."
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- See the television series M.A.S.H. for an example of a cross-dresser who didn't want to serve in the military (Max Klinger). Although the character was played for laughs, his situation was based on military regulations prohibiting cross-dressing.
- Transformation magazine; interviews for Rainbow Reader, Fort Wayne, Indiana
- Jamie Clifton (August 30, 2011). "Female Masking". Vice Style. Archived from the original on July 17, 2012. Retrieved 2012-02-07.
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- Butler, Judith, Gender Trouble: Feminism and the Subversion of Identity, Routledge, New York, 2008
- Halberstam, Judith, Female Masculinity, Duke University Press, Durham and London, 1998
- Epstein, Julia, Straub, Kristina; Eds, Body Guards: The Cultural Politics of Gender Ambiguity, Routledge, London, 1991
- "A Survey of LGBT Americans - Chapter 2: Social Acceptance". Pew Research Center’s Social & Demographic Trends Project. 2013-06-13. Retrieved 2018-03-07.
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- Chesser, Lucy. Parting with My Sex: Cross-dressing, Inversion and Sexuality in Australian Cultural Life, Sydney University Press, Sydney, 2008. ISBN 978-1-920898-31-1.
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- Gravois, Valory. Cherry Single, Alchemist/Light Publishing, 1997 (Available to read free, online), ISBN 0-9600650-5-9
- Leigh, Lacey. Out & About: The Emancipated Crossdresser, Double Star Press, 2002. ISBN 0-9716680-0-0.
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- Simon, Nick. "My exotic life as a traditional Polynesian 'third gender' cross-dresser" Daily Mail