Yessss!!!
I think my first trip to therapy properly dressed was only my third time doing so publically. I was on 2 antianxiety drugs at the time and pre-HRT, laser, electro, coming out, etc. My therapist basically double dog dared me to do it, as she knew I only dressed privately but wanted desperately to interact with the world as Jill. I was nervous, full of self-doubt and I wasn't looking too femme at the time. I assumed a worst case scenario, but it never happened. Nobody even noticed or seemed to care.
I am thankful that I am one to push myself and accept challenges. I'm glad I did it, making that first step, and in doing so I learned a lot about myself and where this path would lead me.
Every time you leave the house as your true self, it just gets easier. Eventually it just becomes second nature.