Sometimes, the first step on the way to a gender transition was to play with gender as performance, art, a kink, or for fun. This low-commitment way to explore how one felt in the literal shoes of the opposite gender was not always a stepping stone to medically transitioning, but many people who pursed medical gender alterations started out with gender atypical dress as a hobby.
[1] “Guests at the Garden Party,” photograph, 1988, Digital Transgender Archive, https://www.digitaltransgenderarchive.net/files/1n79h456k.