Ok, so I'm not the most stylish of people, but I don't like looking like an idiot either. I match my shoes and my belts, my socks to my pants, and I try to keep my fly zipped (in public anyway).
I have a very nice black fedora with that I would like to wear more often, but it just seems so formal. It's a shame, because outside of special occasions, I don't have much opportunity to dress up.
Also, I've looked but I can't find any rules that say your hat should match anything else. Are there rules? What are the rules? Should it match the coat? What if you're not wearing a coat? Are there any black/brown rules that apply?
Why is is so hard to wear a hat these days?