Plinky asked, "What type of hat suits your personality best? A baseball cap? Fedora? Beanie?"
Hmm. I don't know the names of many types of hats, but a cloche comes to mind. I don't own one, but I'd like to. I have my baseball cap and Fedora days, certainly. No matter how geeky I am, I don't think a beanie would suit me.
I do have a purple Sunday-go-to-meeting hat that definitely suits me, but I have no idea what the name of its style is. I'll have to post a picture of it at some point to see what y'all think of it.