I am in my early 40s and older I am, more I want to dress. Nowadays I wear male clothes only for work and when I go out during the day or with friends, since I'm single and live alone. I'm still in the closet and likely will stay like that, except if I get caught and word gets around. But my occasional night walks in the other part of town become throughout last few years much more frequent and I underdress all the time now, even for work and going out with friends.
I even underdressed last time I went on a date too. I tough if she decide to invite me home and undress me on a first date, she is probably enough open minded she might accept crossdressing. If she won't, at least I won't waste extra time on her to find out much latter she hates this. Five years ago this kind of behaviour would be unthinkable for me.