Hats are quite possibly the most difficult accessories to pull off because there are really no rules about them. For example, I can tell you with full confidence that when trying to look smart the colour of your belt should always match that of your shoes. With hats, all rules of the sort go flying out the window. Your hat also has greater definitive abilities than any other accessory you own. For instance, if you want to give the impression that you don’t place to much importance on the way you look, a bright yellow pompom hat will probably do the trick. Or if you want to give the impression that you’re an indie man through and through a well-fitting fedora will do (felt in winter and straw in summer).
When choosing a hat you must either think carefully about it or not think about it at all. Whatever your decision, you must be extremely comfortable with your hat because if you’re not anyone will be able to tell that hats aren’t really your thing and they will immediately assume that you’re going through an identity crisis.
The secret to pulling off any casual hat is to embrace any clash that ensues from its placement on your forehead. Keep it simple, keep it comfortable and most importantly make sure that it is you.