The thing is, I don't think I've ever worn a hat and regretted it (except maybe today when the wind stole it and sent it careening halfway across the parking lot, but that really has nothing to do with any sort of fashion aspect). So maybe there's a lesson there: a lesson to stop fretting over silly things, and to take chances--even small ones--just to push yourself out of your comfort zones.
Outfit details: literally everything: Forever 21. Whoops. :)