From Homestar Runner Wiki
A Bowler Hat is the hat of choice for Homsar, but are also popular among some other people in Free Country, USA. His hat moves around all on its own every time Homsar speaks, but it almost always returns to its resting place on his head shortly thereafter, even if Homsar is standing upside-down (except in different town, as Modestly Hot Homsar, the paper, mini-golf, and origins). A rather amusing example of this is seen in A Folky Tale, where his hat floats in a rectangular path off his head and comes back to the upside-down Homsar. It has also been known to change shape (in his character video) and appear from nowhere (in impression). When Homsar was first created, the hat was much larger and didn't fly as often.
 Other Bowler Hats
- Meet Marshie — The meal "Pinner" consists of Fluffy Puff Marshmallows with a cigar, an eyepatch, and a bowler hat.
- Email dangeresque 3 — Perducci, played by The King of Town, wears a bowler hat.
- Mr. Shmallow — Mr. Bossman wears a bowler hat.
- Teen Girl Squad Issue 8 — In one scene, Cheerleader has on a bowler derby hat, sunglasses, a mustache, a tie, and a cigar.
- Email garage sale — The logo for "The Haggler" has a bowler hat on it.
- Sketchbook — pipestache and strongbones shows a representation of Strong Bad wearing a bowler hat.
- Email yes, wrestling — The Cheat, as the Insidious Mr. Cheatayama, wears a black bowler hat.
- Strong Badia the Free — The icon for trying to speak Homsar's language when talking to him shows Strong Bad wearing a Bowler Hat like Homsar's.