I have a gender therapist, and he "got" me right away, on two fronts. He understood the trans thing without any coaching, but we also connected personally. I think it's a match made in heaven.
If you have access to a gender therapist, great. See if that works for you. But some people are happier with a non-gender therapist (that sounds funny) that they can really connect to on a personal/emotional level. Screen the therapist on the phone if you can, to get a sense of him or her. Switch to another therapist if you don't think the first one is right for you.
Wear what you're comfortable with when you're comfortable with it. If you're FTM, you won't have to worry that people will level judgments like "man in a dress."