Transvestism, commonly termed as cross-dressing, means to dress in the clothing of opposite sex. We describe a series of three cases with transvestism as one of their primary complaints. The discussion sheds light on the various ways in which transvestism as a symptom can present in Psychiatry. In the first two cases, there was lower intelligence. In first and third case, there were other paraphilia along with transvestism. Second case had co-morbid obsessive-compulsive disorder (OCD) and had good response to selective serotonin reuptake inhibitor (SSRI).