Transvestism, which in our civilization seems to have a simple and one-way meaning, is proved to be a very general and vague term, when included in the cultural and social content of other people and placed under different historical conditions. Transvestism, in general, is defined as the total or partial adoption of dress, behavior, way of speaking and works of the opposite sex. The argument that transvestism can have different reasons and cultural content and that it is not necessarily connected with homosexuality is documented through a brief presentation of certain selected and characteristic examples. The concept of transvestism obliges us to exceed the biological sex, social sex, sexuality and reproduction, in order to adopt an attitude that takes under consideration the cultural and social components of each meaning and their interrelation.