Deane: Thanks for asking the question. It sure raises some people's hackles, but I'm like you, mustache too. At home I dress in women's clothes, jewelry, and heels but don't try to look like a woman, although I've gotten more femme as time goes on. My wife is cool with my current situation and sometimes draws my attention to clothes, jewelry, or purses I might like. But to your question:
I started wearing androgynous-looking women's shoes with 2-3" heels in the '90s and carried a small "man bag" but didn't go further. I got laughed at once in a mall and it made me chicken out, although I did confront my detractors. Last year I started hiking in a short skirt but otherwise male presentation. It was amazing! On hot days it felt so liberating to be free of the inseam and feel the air between my thighs. This winter I hiked in women's tights. Got a couple of uncomprehending looks from guys but the women were OK with it. Gradually I've gone out - and to work - in more and more jewelry (gemstone necklaces, small earrings, bracelets). People have asked about them and I say I'm just being creative. I'm sure some think I'm gay, but that's their limited thinking. I do yoga in women's colored tights and have had some fun conversations with other male & female yogis about them. It usually makes others get more creative and colorful too. Some people stare but I just own my style and act confident. I can also laugh at myself and that eases people's confusion.
Lately I've wanted to wear wedge-heeled sandals out to the store, etc., but haven't yet. They look great with my skinny jeans and I'm really tempted. I've been wearing dangling earrings out too and had some nice compliments on them.
As others have mentioned, I couldn't pass as a woman without hormones and some surgery and I'm not sure that's my goal anyway. To me it's about gender diversity and not just fitting into (passing) one side or the other of a rigid gender binary. I don't fit into the male binary now or I wouldn't be crossdressing. So I'm trying to express what I am, somewhere in between, without getting the s**t kicked out of me. Baby steps for now but I see more creative expression coming.
Thanks, Gypsy.