The only time I could pass would be if the person who's looking at me was so engrossed with their own thoughts that they only registered the fact that someone was there as they passed by me. Yet, I go out in various types of women's clothing... Skirts and blouses, dresses, Capri pants and other types of obvious women's pants... women's shoes ranging from sandals through flat to heels. Always with an obvious bust line, make up and earrings. Not to mention my newly acquired women's glasses, which I wear out even when dressed in drab.

..

I have yet to feel like anyone has a problem with me. Our local Safeway and Bi-mart have employees that seem to like talking to me when I'm en femme. All the tellers at the local branch of BofA know me and aren't surprised to see my feminine presentation. Even my doctor doesn't bat an eyelash when I show up in women's clothes.

Only at work and church do I tone it down enough for people not to notice I'm wearing women's clothes. Other than that, anyone who looks at me can tell I'm wearing women's clothes.

I'd say go for the skirt and maybe even more.