I very often wear "feminine" clothing as a male. There is no question I am male.
Yesterday I was able to wear my spandex jeans for work, due to the heat we were having around here made wearing jeans really uncomfortable. I move about in my new job and the jeans were just dragging against my legs, not to mention despite the fact they fit they kept needing to be tugged up.
So I asked my boss (who knows me even before I got the job, I was a regular customer, and the machine I am using to post this is one of his creations), if I could wear my leggings, to which he said "of course".
So yesterday I wore my SDJs. It felt great, and I had to adjust them I think maybe 3 times. They moved with me opposed to against me, and that was nice.
I have also gone out skirted, but my look is usually a bit softer when I do that, just in case I need to "pass just barely" as a female.
Then of course there are the times I go out in androgynous mode But to too many that is a foreign concept.