Jason,
Obviously, I'm not against the idea of men wearing skirts and dresses as men, however since you are asking honestly about your look, I have to admit that even though it is of a similar philosophy to mine, i'm not a fan of it.
It's not the fact that you're wearing dresses and skirts a man that I don't like, it's that from an aesthetic standpoint I don't think the items you're wearing are flattering to your body. Skirted garments can look great on men and there are lots of historical examples to back that up, but many of the clothes made today for women are designed to highlight and play up the female shape in a way that looks odd on the male body. For folks that dress en femme, there are forms and padding to help adjust for this, but if you're trying to present as male, it can look awkward and bulky.
I struggled with this for a long time, and still have to do a lot of work to put together good looking "man in skirt" outfits, though I think I've been fairly successful with it. I've yet to really cross that bridge with dresses though. Typically women's tops and dresses don't work with my shoulders and lack of breasts. I found a shirt dress ad old navy last fall that almost worked but just didn't quite get there.
