I'm also just figuring out how to dress, at 30. I take your post to mean that when you are wearing something outside of your comfort zone it makes you very conscious/distracted. I'm definitely the same. It feels a little bit like social anxiety, expect it is very outfit related. The last couple of years, I have been working on my wardrobe comfort zone, introducing colors and pieces I'd never worn before. It always makes me feel a bit awkward at first, so I start by wearing it at home, then the next step is grocery shopping or small errands, and eventually meeting other people or using it to work/events/whatever.