I have been told all throughout my life that I looked like a girl/woman. Even pre HRT I was constantly called ma'am/she/her/etc.... In fact, when I started college I was going to start the transition process back then, so I started going by my middle name, (which happens to be Ashley) and everyone in my classes just thought I was a girl. My now wife (we were just dating at the time) and I were going to the same college and taking the same courses and during spring break of that year we got married. Right before spring break, we were talking to some of our classmates about what we were going to do during spring break. We mentioned we were getting married. To that one of them said, "That is so awesome. I don't understand why people have such a problem with gay marriage. If two people love each other they should be allowed to express it however they want to."
With all that, you would think I wouldn't question how I looked. The problem is, I really didn't see it. I had my days where I would look in the mirror and see a femish look to myself, but for the most part I only saw a guy in the mirror. I think we always see the worst in ourselves. We see the things that are male about ourselves that others would probably not notice. The funny thing is, now I'm 6 months on HRT and I think I look less fem now than I did before I started. I'm not even sure if that's possible.
The point is, I think most of us will always question how we look to some degree. No matter what we do or what happens to reassure us of how we look, we still don't see it.