I had a rule that I HAD to be consistent with who I was throughout transition... at least as much as possible. Clothing-wise, whatever I wore to work was what I wore at home, when shopping, to therapy, etc. It just became increasingly feminine over time.
I got kinda lucky with the name thing, as I came out at work pretty early-on, and many of my coworkers took it upon themselves to start calling me Kate on their own. Friends, neighbors and relatives too. So that too just sorta evolved on it's own, long before it was my legal name.
The most awkward thing was having to use my legal (male) name when dealing with doctors, health insurance, dentists, etc. I soon got sick of it all though, and just asked each of them to make a note to call me Kate from now on, but use the legal name for claims or whatever. And everyone was just fine with that.
Part of the reason I transitioned when I did was because I WAS going insane, being torn in two by who I was... and who I was expected to be. I just couldn't do it anymore, and became truly frightened by some of the tangents my mind was taking. So I resolved to do everything I could to reverse that trend, to *consolodate* rather than fragment any further, and to reclaim my life and identity.
~Kate~