As sideways baseball hats wane from the spotlight, other options for a bro’s chapeau emerge, such as the now commonplace fedora or the traditional skull cap. The most important thing to think about is your head (not surprisingly). If you have a big noggin but are wearing a tiny hat, people are either going to think you’re a goofball or that you have gigantism. At the same time, if your hat is too loose and falling over your eyes like some little leaguer, no one’s going to take you seriously. Spend some time figuring out the best size and style for your noodle. You’ll be glad that you did.