Rachel,
I would put Confidence and lack of Paranoia up with the key things that go with a sucessful transition.
No matter how well you pass, your voice sounds, attracting undue attention is not what any of us want. This brings stress, undue pressure and you can in a second blow anyones perception of how they view you.
I went through a phase when anyone looked at me, smiled or nodded, I went into defensive mode,assuming I had been read, or people where inwardly laughing at me, that was never the case, just my own Paranoia.
You feel happy and secure in what is effectively androgynous clothes, but you cant spend the rest of your life wearing these, fine as a student, but venture out into the World of work and that is not what normal women will wear.
Only you can work through these problems. Admitting you have a problem is a big step and I know that you have not seen a Physchiatrist or had counselloring yet, this is an important point to discuss. It is like any fear, it can be overcome, but you have to find that deep inner strength to do so and take that leap of faith.
This is not about clothes, but about your perception of how you appear to others, thats what you need to work on, gaining the confidence that people do see a woman and losing the paranoia that they dont.
Buffy
(Who went through the same issues)