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Cross-dressing is the act of wearing the clothing of another gender for any reason. The usage of the term, the types of cross-dressing both in modern times and throughout history, an analysis of the behaviour and historical examples are discussed in the article below.

Contrary to widespread societal views and prejudices associated with cross-dressing, most people who cross-dress do not do so for sexual or fetishist reasons. Similarly, although cross-dressing is one type of transgender behaviour, most cross-dressing is not caused by transgender feelings or identity. Most cross-dressers are not gay.

Nearly every human society throughout history has distinguished between male and female gender by the style, colour or type of clothing they wear and has had a set of norms, views, guidelines, or even laws defining what type of clothing is appropriate for each gender. Cross-dressing is a behaviour which runs significantly counter to those norms and therefore can be seen as a type of transgender behavior. It does not, however, often indicate transgender identity; a person who cross-dresses usually does not identify as having a gender different from that assigned at birth.

The term cross-dressing denotes an action or a behaviour without attributing or proposing causes for that behaviour. However, some people automatically connect cross-dressing behaviour to transgender identity or sexual, fetishist, and homosexual behaviour. Referring to a person as a cross-dresser suggests that their cross-dressing behaviour is habitual and may be taken to mean that the person identifies as transgendered. The term cross-dresser should therefore be used with care to avoid causing misunderstanding or offense.

There are many different kinds of cross-dressing, and many different reasons why an individual might engage in cross-dressing behaviour.

Some people cross-dress as a matter of comfort or style. They have a preference towards clothing which is only marketed to or associated with the opposite sex. In this case, a persons cross-dressing may or may not be visible to other people.

Some people cross-dress in order to shock others or challenge social norms.

Both men and women may cross-dress in order to disguise their true identity. Historically, some women have cross-dressed in order to take up male-dominated or male-exclusive professions, such as military service. Conversely, some men have cross-dressed in order to escape from mandatory military service.

Single-sex theatrical troupes often have some performers cross-dress in order to play roles written for members of the opposite sex. Cross-dressing, particularly the depiction of males wearing dresses, is often used for comic effect onstage and onscreen. In pantomimes, ballet and even opera, some roles are traditionally played as “travesty” (cross-dressing).

Drag is a special form of performance art based on cross-dressing. A drag queen is usually a male 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 employing the same techniques.

A drag king is a counterpart of the drag queen but usually for very different audiences: a female (often lesbians) who adopt a masculine persona in performance or imitates a male film or pop-music star. Some female-bodied people undergoing gender reassignment therapy also self-identify as drag kings although this use of “drag king” would generally be considered inaccurate.

Transgendered people who are undergoing or have undergone gender reassignment therapy are usually not regarded as cross-dressing. A transsexual who has completed gender reassignment surgery is certainly not considered cross-dressing, unless they were to wear clothes of the gender opposite of what they have become. Pre-operative transsexuals may be considered similarly.

A transvestic fetishist is a person (typically a heterosexual male) who cross-dresses as part of a sexual fetish.

The term underdressing is used by male cross-dressers to describe wearing female undergarments under their male clothes. The famous low-budget filmmaker Edward D. Wood, Jr. said he often wore womens underwear under his military uniform during World War II.

Some people who cross-dress may endeavour to project a complete impression of belonging to another gender, down to 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-dressers attempt to pass is said to have read them. There are books and magazines on how a man may look more like a woman.

Sometimes one a heterosexual couple will wear it to arouse the other. For example, the male would wear skirts or lingerie and/or the female will wear boxers or other male clothing.

Cross-dressers may begin wearing their opposite sexs clothing as children, 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 behaviour. Cross-dressers may become obsessive and/or compulsive in their behaviour, if not actually addicted to wearing the opposite sexs clothing. Some have periodically disposed of all their clothing, a practice called “purging”, only to start another collection later.