I occasionally wear a skirt and make up, but it's not nearly as fun as when I was younger, and when the result of the dress-up effort was looking hot and sexy.
Now older, with hot and sexy not an option, I wear the same thing every single day. Jeans, trainers and a top. No make up. I can see how this wouldn't do the trick for a trans-'woman'. They have to put on makeup and dress carefully to live the fantasy. And Jenner thinks it's what we all do, that we all care about looking feminine, but he's wrong.
I've read of some trans-'women' saying they worry about being an ugly woman after they 'transition'. That's the sort of thing a man would worry about. Because we all know, all real women are fuckable.