I hide my dressing because I could never pass, and I think I'd lose a lot of friends if I tried. Even before I had a beard, the image I presented when full dressed was somewhat like a pregnant grandma. In fact, my exes sister had a Halloween party once with "come as the opposite gender theme, and that is how I dressed. I wore one of my wife's old maternity skirts and top along with a grey haired grannie wig.
If I could dress with no repercussions from family, friends, or anyone else, I'd never wear anything but feminine clothing.