Vain concerns about transitioning?
I'm middle-age and I'm thinking about transitioning. (m2f) I think I would prefer to be a woman. I'm pretty lucky in that I think my immediate environment would make it comparatively easy. I've talked about it with the most important people in my life and they've all been supportive.
Here's the thing: I feel like it took me decades to find a way to be ok with my appearance as a man. I think I'm cute. I know what kinds of clothes look good on me. I'm overall pretty happy with how I present right now. I'm worried that if I do transition, I am signing up for decades more of finding a new way to be comfortable in my body. Decades of thinking once again that I'm ugly, can't dress well, etc... That would suck.
I'm wondering how others have thought about that and/or are handling it.