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Drag is a term applied to clothing and makeup worn on special occasions for performing or entertaining, unlike those who are transgender or who cross-dress for other reasons.Drag performance includes overall presentation and behavior in addition to clothing and makeup. Drag queens have been considered caricatures of women by second-wave feminism.

The degree to which individuals feel genuine, authentic, and comfortable within their external appearance and accept their genuine identity has been called transgender congruence. Oliven of Columbia University coined the term transgender in his 1965 reference work Sexual Hygiene and Pathology, writing that the term which had previously been used, transsexualism, "is misleading; actually, 'transgenderism' is meant, because sexuality is not a major factor in primary transvestism." By 1992, the International Conference on Transgender Law and Employment Policy defined transgender as an expansive umbrella term including "transsexuals, transgenderists, cross dressers", and anyone transitioning.

Leslie Feinberg's pamphlet, "Transgender Liberation: A Movement Whose Time has Come", circulated in 1992, identified transgender as a term to unify all forms of gender nonconformity; in this way transgender has become synonymous with queer.

Distinctions between the terms transgender and transsexual are commonly based on distinctions between gender (psychological, social) and sex (physical).

Hence, transsexuality may be said to deal more with physical aspects of one's sex, while transgender considerations deal more with one's psychological gender disposition or predisposition, as well as the related social expectations that may accompany a given gender role.

People who cross-dress in public sometimes may have a desire to pass as the opposite gender, so as not to be detected as a cross-dresser.

The term transvestite and the associated outdated term transvestism are conceptually different from the term transvestic fetishism, as transvestic fetishist describes those who intermittently use clothing of the opposite gender for fetishistic purposes.The THP recommends that clinicians ask clients what terminology they prefer, and avoid the term transsexual unless they are sure that a client is comfortable with it.Harry Benjamin invented a classification system for transsexuals and transvestites, called the Sex Orientation Scale (SOS), in which he assigned transsexuals and transvestites to one of six categories based on their reasons for cross-dressing and the relative urgency of their need (if any) for sex reassignment surgery.people who meet Benjamin's definition of a "true transsexual" but do not desire SRS include Miriam Rivera.There are also people who have had SRS but do not meet the definition of "transsexual", such as Gregory Hemingway.For example, Christine Jorgensen publicly rejected transsexual in 1979, and instead identified herself in newsprint as trans-gender, saying, "gender doesn't have to do with bed partners, it has to do with identity." The definitions of both terms have historically been variable.