Ok... what I am about to share is about my experiences over a fairly short period of time.
Firstly, some background. I became aware of being transgender approximately 12 months ago. The first person I told was my wife... fortunately our relationship is incredibly strong, very communicative and large helpings of trust. My wife also identifies as pansexual so, she still loves and is attracted to me for whom I am inside. I am incredibly lucky, it was however a very difficult thing to put out there.
My wife supported me by taking me shopping and helping me through the learning curve of women's clothing and fashion. Although my hand was literally being held through this, I felt a lot of anxiety and embarrassment about looking for and trying on women's clothes. The anxiety has never completely gone away, but I find it very manageable going shopping for clothes/underwear etc by myself now. I still have a lot to learn about fashion/matching/colours.
Late December 2015 - I went out in public for the first time dressed in women's clothing (no makeup). It was a mix of achievement, fear and exhilaration. I swear I could feel everyone's eyeballs fixed on me everywhere I was... I struggled to look up. Later on, when I got home I felt so amazing! I didnt actually die of embarrassment!
I know that the first, second and even tenth time going out in public dressed differently can feel very awkward. However, it does get better. So by mid January I was living womanly full time (with the exception of work related travel and appearances). I still felt the "eyeballs" on me, wherever I went. So I really analysed this feeling I got and discovered something... It wasnt just a feeling, but I was seeing them look, but we all glance at each other every day... at the supermarket, in the street, in the office. My paranoid mind was turning these glances into "they are looking at me because im transgender and dont pass".
At the end of the day, the vast majority of people that I encounter in public, I dont know and I probably wont ever see again. I started reciting a mantra when I was out and feeling/seeing the "eyeballs". It was simply: "Get on with it" and "I dont know them, they dont know me". What I found is that if I was "looking" for people that were looking at me, I found them. As soon as I stopped looking for it, I found that I really was just "getting on with it".
In my opinion, I dont pass. Maybe sometime in the future I will. However, Its not something I can base my happiness being who I am on. Of course I'd love to look convincing, and initially this was something that I wanted to achieve before I went out in public... the fact is that priority needs to be adjusted.
Ive found I have more time to think about other things when I am out. I was in the early days consumed by the feeling of the "eyeballs" that I'd sometimes forget where I was, what I was doing there, and what I needed.
I do attend therapy, and some of this progress is attributed to that. However I didnt get to where I am instantly. I am now in the midst of my workplace transition and I feel strong and confident. I hope that my experiences and opinions help some of you with your daily struggles.