Congratulations on moving to a better situation.
How to present yourself is a very personal decision. It is really what you are ready for and how comfortable you are pushing your personal limits. You need to get a little bit beyond your comfort level, otherwise you can't grow. But you don't want to freak yourself out from fear, either. Find your own balance.
I started dressing and going out in public part-time first, after a makeup lesson from a friend. I did that for several months before starting HRT. Now, three months into HRT, I am full-time. Going out the first few times was scary, but I stayed in control and enjoyed it, and nothing bad happened.