This article examines the case files of patients diagnosed with Transvestitismus [transvestism] in the Psychiatric Clinic of the Helsinki University Central Hospital in the years 1954–68. These individuals did not only want to cross-dress, but also had a strong feeling of being of a different sex from their assigned one. The scientific concept of transsexuality had begun to take form, and this knowledge reached Finland in phases. The case files of the transvestism patients show that they were highly aware of their condition and were very capable of describing it, even if they had no medical name for it. Psychiatrists were willing to engage in dialogue with the patients, and did not treat them as passive objects of study. Although some patients felt that they had been helped, many left the institution as frustrated, angered or desperate as before. They had sought medical help in the hope of having their bodies altered to correspond to their identity, but the Clinic psychiatrists insisted on seeing the problem in psychiatric terms and did not recommend surgical or hormonal treatments in most cases. This attitude would gradually change over the course of the 1970s and 1980s.