The question of transvestite fashion (dated statement) is, as Marjorie Garber has noted, the essence of theater, role playing, costume, and boundary experimentation, the qualities so evident in the aesthetic celebrity in such people as Oscar Wilde.
In 1882 one of the highly praised and best-paid minstrel star was the female impersonator Francis Leon, who boasted that he owned three hundred dresses and a great deal of jewelry.
In vaudeville, female stars appeared as Oscar Wilde (“silk stockings, knee-breeches and a velvet coat”), an indication that the experiments within aesthetic iconography (theater, self-creation, and new personal presentations) were extending into an arena of popular entertainment.
Male drag is a staple of theatrical and cinematic tradition. Examples range from the famous stage performances of Sarah Bernhardt as Hamlet and (more recently) Pat Carroll as Falstaff, to the operatic convention of travesti or “trouser roles” in which mezzosopranos sing male roles, to the memorable presences in male attire of movie actresses as varied as Clara Bow, Greta Garbo, Marlene Dietrich, Katharine Hepburn, and Julie Andrews. Some entertainers, such as blues singer Gladys Bentley, who sang about “bulldaggers,” while dressed in tails and tuxedo, sexualize the cross-dressing. Although cross-dressing always has a potential to destabilize assumptions about gender and sexuality, the impersonation of men, even by black lesbians, has usually not been seen as threatening when presented as entertainment. Consequently, drag kings are usually greeted with enthusiasm even by predominantly heterosexual audiences.