I couldn't escape being photographed while I lived with my parents, but I ducked the camera at every opportunity when I was an independent adult. So I don't have many pics to look at from my twenties.
A couple of years ago, I needed a childhood photo suitable for public consumption. I found one that was sufficiently androgynous, and I was happy with my choice. But while I was rummaging around, I ran across a few pics from my twenties. I remembered myself as physically unappealing, especially because of a chronic skin condition I had. But I stumbled across a candid photo that a friend's mother had taken. I was wearing my ugly backup glasses (something had happened to my first pair), and the skin condition wasn't visible. I suddenly thought, "Gee, she's kinda cute if unconventional-looking."
I tend to like distinctive-looking people, not the cookie-cutter conventional looks of so many people who are considered attractive by others. I'm not into women at all, but I had finally achieved enough distance to recognize that my twentysomething self wasn't hideous, just unhappy and lost.
For a little while after my transition, I thought I wasn't bad looking. But that period didn't last; I don't have a very high opinion of my looks at this stage of my life. Maybe I'm so down on myself because I'm struggling again. Also, my hairline has receded a great deal, my face shows visible sun damage (I have incredibly sensitive skin), and I'm disabled now and can't work out and lose the extra weight. Still, I wonder if I'll find a male pic of me in twenty years (happier days, I hope) and think, "Hey, not bad." Maybe I'm looking at myself now through a jaundiced lens.