Guys, pay close attention because this is where things can go horribly wrong. When choosing a hat consider the shape of your face, your complexion, the outfit you’ll be matching it with and the material the hat is made of. Just like with clothes, men should apply the same rules when selecting headgear. “A lot of guys buy hats too big and look like a kid wearing their father’s hat,” says Derek Roche, personal stylist to Sean “Diddy” Combs. Roche stands by “fit and style” when choosing the right shape and style of hat. “Make sure it fits the aesthetic of your clothes. You’re not going to wear a New York Yankee fitted cap with a Dior suit.” Unless, of course, you’re Russell Simmons.
If you have a round face, you want a hat to add some length, not make your mug look rounder. You would look your best with a hat that has a medium crown and medium taper. The band should be thin and contrast in color. This combination will provide a slim look and even add some height. The brim should be slight to moderate in width in order to contribute to the elongation.
Long or Thin Faces
If your dome is on the long or thin side stay away from square crowns and go for a small to medium crown and taper also go wide with the band. This will help give your face a more compact look. Opt for a moderate to wide brim to help reduce the vertical look.
Square faced/jawed gents should pick a medium to full crown with virtually no taper and the brim should be wide. These cuts should add some curvature to your mug and make it appear less boxy.