I grew up in the 50s-70s. A lot of people my age have not moved past "I'm cis and anything non-cis is bad". Beliefs we're taught as children often stick with us on a primal level. It was worldwide news when Christine Jorgensen had the first modern SRS in the early 50s, and the general public thought it was bizarre, scandalous, and scary.
I'm on the committee for my 50th high school reunion, and I just found out that somebody I knew as Tom transitioned decades ago. Warms my heart. I hope Julie (middle name Thomas) comes to the reunion!
Social anxiety is a significant issue for me in drab, thank you very much, so my crossdressing is entirely private. Not even family. I can't imagine me going crossdressed to a party of 200+ of my high school classmates, much less going as a woman named Lisa.
A while back my sister told me she'd talked to one of her high school classmates, a transwoman, whose parents used to play cards with ours. She said that when the game was at our house, she was at home "upstairs trying on my sister's clothes". I really wanted to say "ditto", but I'm quite content with things just as they are.