The first time I tried makeup and tried wearing feminine clothes, I cried. And not in a good way.
I cried because when I looked at myself, I just looked like a man dressing up like a woman. I didn't want to be a man dressing up like a woman, I just wanted to be a woman. (And this was over 6 months into HRT.)
And yeah... my dysphoria didn't really ease until I started reaching the point where I was beginning to be gendered female and seeing a girl in the mirror no matter what I was wearing or whether I had any makeup on or not. That was my goal all along. I HATED myself, and felt like a fake, back during the time where I still needed a wig, a padded bra, makeup, and feminine clothes in order to look even remotely feminine. (And even with all of those things on, I still didn't look like a woman to myself, so it REALLY hurt.)