Do you wear hats? If so, how often? If regularly, is it a rotation of hats or just one hat? Some stylistic consistency and seasonal variation are assumed.
How often do you clean your hats?
I wear a black on black wool Fedora. Usually only when I'm dressing up more than everyday, and since I live in Florida definitely not in the summer. Other than that, I'm not much of a hat wearer. I mm looking into some different Fedoras and styles though, as I do appreciate the little bit of flair it adds to a look.
I only own a cheap brown herringbone flat cap. UnfortunateIy life in so cal doesn't give me too many opportunities to don it. However, when I studied abroad in Oxford last fall I I wore it nearly everyday. I'll probably upgrade it in the future to something of the same style but made with nicer materials and better construction.