One's teen years are full of questioning and impression forming. Mine were in the 1950s and early 60s. I hadn't heard of crossdressing and "transvestite" was a term used only as abuse. Nevertheless, I remember as an only child being intrigued by the very different clothes worn by girls my age - and older. I constantly wondered about how girls would be feeling as they walked to school in their skirts and dresses and I was very aware of the significance of the lingerie and underwear they wore, even though it could only be seen in catalogues, shop windows and on washing lines. The curiosity was such that I had to try it but resources for doing so were very limited. Only when I was old enough to have real girlfriends and to get close to them did I begin to find out exaclty what they wore and learn about their own experiences of those clothes. Female clothes then were so much more complicated and varied than male clothes and therefore fascinating - I wanted to try them just to find out what it felt like to be dressed like them. The endless variety not only of skirts, dresses and shoes (trousers almost unknown for women then) was easily observed every day (I watched girls trying to manage big skirts held out with stiffened slips, trying to run in heels or climb the stairs on the bus in a tight skirt and wanted to try those things for myself) but less visible were the numerous types of stockings, bras, suspender belts and girdles which they were all wearing under those clothes. I spent much time wondering what it must be like to wear those things all day and every day....something I couldn't experience but could just glimpse in my own hurried, closeted dressing sessions.
I'm afraid the enthusiasm waned with later fashion styles and is now absent altogether when almost all women and girls dress only in casual things, trousers, trainers, leggings, etc. Of course, I understand that those younger than I are just as intrigued by the female clothes that surrounded them in their own adolescent years and that those males wanting to go out into the world as women want and need to follow the clothing trends appropriate to the period and the place. For me, though, there's no doubt that the 50s and 60s were very influential.