#5 Timberland 6" Premium Boot "10061"
Dallas says: "Don't get it twisted, internets — this boot might be the most Hip-Hop sneaker of all time. Even more than the Air Force 1 and the adidas Superstar since this boot gets worn in four seasons in every weather condition. I can promise you right now there is a dude in Brooklyn playing basketball in these as well as a Puerto Rican in the Bronx playing handball wearing these cheese boots. That shit kray."