I am one of "those" transsexuals who did not do a lot of dressing before she started hormonal transition. I want to use this post to try to shed some light on why that is/how that works, at least in my case.
I developed a distaste for most forms of crossdressing as a young adult because I did not like the way female clothes hung on my male looking body. So instead I sought out male analogs for female clothing, such as men's bikini underwear, tank tops, speedo type swimsuits, etc.
My current transition is not my first attempt -- it is my fourth. I researched transition and made long distance calls to doctors back in 1982 when I was in college. The lack of funds stopped that effort. I self diagnosed and made a second attempt at transition after I finished law school in 1989, but stopped when I read that "Gender Identity Disorder" what they called it back then, was considered a mental illness, and a diagnosis might result in the loss of my law license. On my third attempt in 1998/1999 I was crossdressing at home, had a female online persona, and was just starting to explore myself when I went to court one day and saw a young transgender girl get mistreated by a judge. That ended attempt #3.
In 2005 I started having chest pains, irregular heartbeats and high blood pressure, and my doctors kept telling me it was work related panic attacks. I passed all the cardiac tests. My doctors tried anti depressants, beta blockers, tranquilizers, and anti anxiety drugs, and nothing worked. Near the end of that (late 2015) two things happened. 1) My panic attacks turned into a nasty stress related disorder called Roemheld Syndrome, where nerve impulses and spasms from my esophagus were messing with my heart and causing tachycardia and actual cardiac pains, and 2) I learned almost by accident that cross dressing would stop a panic attack dead in its tracks.
I managed to survive for a year as an at home cross dresser, but I still did not like the way the clothes hung on my male body. At the end of that year I was almost housebound by the panic attacks. That is when I went in for gender therapy. Hormones fixed almost everything. I was still having mild to moderate panic attacks every time I had to put the men's business suit on and drive to work like that, but other than that, I knew real happiness for the first time in my life. Now, after 17 moths on hormones, my face and body are totally different, my (female) clothes fit like they were meant to, and I am a happy girl, living full time except when I have to go to court (2 days a week, usually) and when I have to visit relatives I am not out to.
I am getting ready to legally change my name and gender, then I can change my name and gender with the state bar, and go to court as me, rather than as "that guy."
I have learned the hard way through trial and error, that this is not really about the clothing, or even the way my body looks. If my hormones are off, then I can get anxious and irritable and panicky and all the old bad feelings can come back. Up until coming out to myself I never thought of myself as a female because I was never allowed to by my parents. But the bottom line is, I function far better in society and I feel far better about myself living as a woman, and there definitely is a hormonal component to it.
So, this is me. Hugs, Carly