I do remember as a child/teen wondering why 'transexuals' as they were in those days, always wore what I thought was quite old fashioned frumpy looking clothing, so skirts and dresses and court shoes.
Whereas me and my friends were wearing funky brogues, doc martins, jeans, cropped hair, boxy jackets, that sort of thing
I see now that they were wearing 'womens' clothing in their eyes. So this has always happened it seems.