When I came out to my friends in 2006 they were eager to dress me up lol. It was in October so I mostly did it to prep for a big Halloween festival where I dressed up as a 'sexy witch'. I had a long black skirt and a corset, witch hat, etc. When I was trying things out before that, I was a bit apprehensive. Sure buying some clothes (like a bra) was exciting, but actually wearing things and wearing some horribly done make-up made me feel awkward and uncomfortable. I naturally look a bit femmy, or at least not masculine, but I still felt like it was all completely transparent. But when it was showtime and I was all dressed up to go out, I felt almost euphoric and a lot more confident. Sure I wasn't passable, but I was out in public wearing women's clothes and being Halloween, nobody cared! Some people said I looked good and took pics with me. And at one point, walking along the side of the road to my friend's house, someone drove by and made with the cat calls. It felt good. Even spending the day in a corset and having a mild panic attack when I had to choose between the restrooms, I was happy and comfortable. But after that, I only dressed up a few times. In retrospect, I should have been more embarrassed than I was, but in a way I felt defiant when I was out in public with a stuffed bra, women's clothes, and some make-up.
After all that I shoved everything in the back of my closet. What remained was subtle, like earrings and some hair-clips because I was hiding it all from my parents. I stopped hanging out with my friends for unrelated reasons, and had no reason to go out most of the time. Spending a lot of time in virtual worlds, I ended up dressing up avatars as an outlet. I did get a bit daring once when I went with my parents on vacation. I carried around a small 'travel bag' which I used as a purse. It was light blue but very purse-like, but my parents never said anything about it. And once, at a restaurant, I was carrying it and wore a red v-neck shirt and my hair was long and a waiter ma'am'd me. Was a proud moment lol.
So yes, I've felt this way at times. I figured when I finally got to transition I would feel more comfortable dressing up. Right now I'm at one month on HRT and had one laser session so I'm not quite ready yet but I did recently buy some cute pink fuzzy jammie pants. Refraining from buying anything else until I get in better shape. xD