get comfortable going out by myself

I don’t really like to go shopping by myself, because I can get to doubting how something looks good on me. A few days ago, I was going to buy grey jeans because they do look good/cute, but I know it doesn’t quite match other stuff I have, mainly the 1 jacket that I have and wear like every day. In other ways of going out, I don’t like to look like I have nothing to do (a flaw, I know). I am comfortable standing around listening to my music though, interestingly enough.