Headgear
From Homestar Runner Wiki
Most of the characters have worn a hat at some time or another, usually of very different styles. Homestar Runner wears a propeller cap, Homsar wears a bowler, and Coach Z wears a baseball cap (backwards) all the time. In the photobooth in Strong Bad's Cool Game for Attractive People, Strong Bad can wear a wide selection of headgear. In Where My Hat Is At?, Homestar loses his hat and later finds it in his refrigerator next to some cold ones. The Broternal Order of Different Helmets wear a wide variety of helmets.
In addition to hats, other headgear is sometimes seen. For example, The King of Town wears a crown, and Homestar wears a bowl on his head when he is part of the Homestarmy. Strong Bad's painting of a guy with a big knife wears a headband a lot like Rambo's.