One thing I have thought about is that when one transitions older, one doesn't accumulate the same gradual sense or understanding of what those looks mean as when one goes through puberty and grows to an adult woman. We are learning how to gauge it all. We don't have the trial and error evolution of self and becoming as a woman socially, learning about ourselves and in relation to others. I know adolescents go through hell anyway about it and don't have it "easier" in that they are figuring out who they are. But unless they are T (and I was then too, I know, so it was a mess) it's not at the same level of basic identity as we cope with. We jump in with both feet and have to deal with "where do I fit in on the looks scale as a woman, and why is that man looking at me" at the same time as "I hope I am passing here." On the one hand I feel I am 16 and discovering my body and how others see me, on the other I am asking am I doing something wrong that screams male? By the time a girl grows to be a woman, she has dealt with the self doubt and "boys." She generally knows the "rules" and what is a reaction to her, and what is simply someone admiring how she dresses or that she simply stands out as tall or whatever. She also knows how to cause reaction, I suppose, or avoid it. I feel I have all the insecurities of an adolescent with the all the worst case scenario imaginings of a middle aged person with "experience."
I think I have this notion I'll have that one compliment or experience that "validates" or reassures me, where the look is somehow explained. This is nonsense. But I hope for an epiphany. And I suppose for every "look" that causes doubt there is a compliment or smile that cancels it out in the great scheme of things. Transition karma or something like that. That might be a healthier way of looking at it. But I excel at self doubt.
One problem I find is that I have a ton of female friends, but nearly no male ones and no close ones anymore. It was that way before transition. My closest female friends say: you look great, you know what we do about clothes, makeup, etc., just enjoy the looks and chalk it up to being the tall athlete. Then again, sometimes their measurement of success is that when we go out we are all ma'amed -- the lack of negative reaction is the threshold. I have no male feedback at all apart from family, and they say "we knew you before, we are terrible judges of all that."