Hats are marks of distinction; they can add an element of character of the wearer. Think Indians Jones and his hat. They’d be no hero there without the hat. The hero is always the one with the hat, riding up in the nick of time. Bear in mind, a good position is everything. Therefore you should rock it at an angle. Whether your face is long, square, round, or a combination, when properly angled, the shadows compliment your better features.
Which hat style looks best on you? Is it a Tribly or porkpie style? This style tends to have a sharp, moderately sized crown, with narrow brim, hense the term stingy-brim, which looks great on a man with a small face and narrow shoulders, say like Sinatra.? Or are you the Homburg or fedora type, which by virtue of their generous brim, add balance for a man with a more medium to wide jaw, full face and broad shouldered. Which ever you choose remember, hats are very visible, and you don’t want your hat to be wearing you. Therefore you should wear it in your correct size; width of hat’s crown should match width of your face. Brim’s width should stay within confines of your shoulders, and rest 3/4 inch above your brow, and no better than 1/4 inch above your ears is the proper fit. And remember to pull it down slightly in the back, to allow your handsome face to be seen.