I've been dressing the way I do for as long as I can remember. High School, I felt was probably my shining moment, my figure was the best it was ever going to be, (36, 28, 42) I went to classes in my boy clothes or girl clothes without a care in the world, and for the most part, nobody else cared either. I was just allowed to exist.
Adulthood was the crushing blow to all that. Suddenly I had to stop being myself, and 'blend in.' Lest I be an 'unemployed failure with no children.' (As my family puts it.)
My therapist explained to me once that a lot of individuals flock to the 'goth' subculture as a sneaky way of cheating their way into presenting more feminine under the radar. There never used to be anything 'under the radar' about me growing up, that came with adulthood. I'm firm in my stance that the way I dress or do my makeup or anything else isn't going to change the minute I have the right body.
I do need more excercize though, and... maybe a diet.