That’s Vermin Supreme, and he’s ran in every Presidential election since 1992. If elected, he promises a pony for every American (presumably like the one in the picture), and to go back in time to kill Hitler before World War II begins. He also has a secret plan to end the inevitable zombie apocalypse. And yes, that’s a boot on his head.

Vermin Love Supreme (born 1960 or in 1961), he is an American performance artist, politician, and activist who has run as a candidate in various local, state, and national elections in the United States. He serves as a member of the Libertarian Party's judicial committee. Supreme is known for wearing a boot as a hat and carrying a large toothbrush, and has said that if elected President of the United States, he will pass a law requiring people to brush their teeth.

P.S: this passes for the political section as well as the joke section, but since it's real, let's leave it in politics.