Originally Posted by bbaquiran
Are there any guidelines, or do you just have to try lots of hats until you find the ones that suit you?
Generally, the size of the brim should be proportional to your head. If you have a tiny head, you don't want a big brim. If you have a massive head, you don't want a tiny brim. Other than that, I can't think of much other than to experiment.
Personally, I find it good when a hat is proportional to what your wearing, too (and of course, it should be appropriate--i.e., no straw hats with flannel in the winter). I think one can carry off a slightly bigger brim than they normally can when wearing a DB suit or an overcoat, for example. But that much is just my own opinion.