I think I got my first heels when I was 16 and able to drive. I went to a Payless shoes, and the only memorable part of that trip was me awkwardly feeling I -had- to spew out my fake back story the clerk did not ask for. I kept those shoes and a stack of Mad magazines in a metal lock box in my closet. I think my parents were worried I was doing something illegal as when I returned from a trip to Michigan the magazines were in my closet, no box or heels.
Sometime in my tween years I figured out something was up with my gender identity. I liked some girl things, and did not understand why your gender limited your life experiences. By 13 I was hitting a crisis point, and decided to just ‘be me’, and live on my own terms. Back around 1990 non-binary was not a thing. If it had I might have been far more comfortable mixing up my appearance in public.