Have you ever seen the classic 80's sitcom "Get A Life"? Hip-hop legend Dan the Automator named one of his first projects "Handsome Boy Modeling School" after a scene from this show. This is the hat that inspired it all and serves as a tribute to Chris Elliott's wacky shenanigans.
This hat is printed on the Otto #39-165 with an adjustable plastic buckle on the back. This is a high-quality silkscreen, not an iron-on transfer.