Every day. I know that I have good days and bad days, all barometers of the "internal weather"...but when I see the infamous "man in a dress", I tell myselves*, "Well, if we don't like it, we can always go back to wearing men's clothes and maybe even taking testosterone again!"
There is an immediate hush from my "inner critic". I may be a man in a dress now, but I'm on the path to be a woman, and I just have to survive this awkward phase I'm in...
*Yes, I do have "inner selves" (plural). They all represent some aspect of "me", the whole person, who is no longer able to present as one. Even I am not the whole person, I am one aspect, which enjoys the cooperation of the others inside.