History: The popular "dress hat" comes in a variety of crown heights, brim lengths and colors. Andler said they typically recommend this hat for first-time buyers.
The fit: Given the range, it's important to buy a fedora that fits with your face shape. If you have a round face, look for a fedora with a moderately wide brim and a medium-height crown. A long face looks best with a shorter crown and a somewhat wide brim. But Don Draper can pull off any fedora style.
Seen on: Justin Timberlake, Bruno Mars, Brad Pitt, Frank Sinatra.Bowler or Derby
History: Popular among bankers and stockbrokers back in the day. Also popular in the Wild West (way back in the day) because it wouldn't blow off in strong winds. The hat had another pop-culture moment when Alex DeLarge and his droogs wore bowlers in "A Clockwork Orange."
The fit: These hats fit best on someone with a long face because the wide brim will help shorten the face's appearance.
Seen on: Prince Harry, Jude Law, Usher, Charlie Chaplin.Cloth caps
History: Also known as newsboy caps, flat caps, driving caps or gatsbys. These caps tend to have less structure than fedoras. According to Heimie's hat guide, caps were reserved for the working class, but today they can be worn formally and are much more common than brimmed or blocked hats.
The fit: Andler said these hats work with almost all face shapes because they are more like a baseball cap, with a tendency to frame the face.
Seen on: Brad Pitt, Paul Newman, Gerard Butler, Tim McGraw, 50 Cent, Samuel L. Jackson.Homburg
History: This hat is a hybrid of a fedora and a bowler. Heimie's describes it as "a hard blocked hat with the fedora's dent along the top and the side-curled brim of a bowler." It's also known as "The Godfather," after Al Pacino wore the hat in the classic film.
The fit: This hat looks best on a square face because it will add some curvature, making the face appear less boxy.
Seen on: Al Pacino, Colin Farrell, Johnny Depp.