Reine, this is an excellent question.
About 4 years ago and slightly before ramping up our respective transitions, I was out with another member of this forum (Badtranny) and she posed a very similar question. There was a large group of women ranging from pretty and well dressed to more "plain" and overweight as compared to the others and less attractive by most societal standards. She asked would you still be one of those women versus one of the more attractive ones. We both answered without hesitation, yes. While it would be nice and desirable to be one of the more pretty women, all we wanted was to be a woman. It was not about the appearance but the essence of being a woman even if far from societal measures of beauty and attractiveness.
For the past three years I have been working in nearly or all female (me included) office work environments. What I enjoy and cherish the most is not being able to "dress up", but the friendships and sense of belonging. In my experiences, friendship between women and friendships between men have a different character. I am blessed with some awesome close friends, and it is our closeness and openness that I value the most. A few know I am trans and others do not, but from what I can tell, it has not made a difference. This is just one example where it is not about looking feminine or appearing as a woman, pretty or not, but about being a woman even if it comes with being far from the feminine ideal. Yes, I would love to be pretty and attractive, but it is (was) not a requirement.