Early on, I used to joke that I couldn't pass my way out of a paper bag, on a good day. At a certain point in my process of discovery I decided that I don't need to pass as anything, people see what they want to see. Some might see a frumpy woman, others might see a man in a dress, I'd guess that some others might not notice or care at all. I can't control anyone's perception of me, all I can control is the way in which I might wish to express my gender, and how I feel about whether or not I pass.
We have all been barraged by negative media perceptions of transpeople our entire lives. I believe that everyone of us carries a certain amount of internalized transphobia, it is our choice to recognize this, and if we choose, to try and overcome it. I also hope (and work) torwards a future day in which it is OK not have to "pass", when it will OK to openly and safely express ones gender, wherever on the continuum it might be.
zythyra