Flat-soled shoes and durable, stretchy skateboarding clothing help skaters land tricks. Skateboarding is a lower-body sport, and your pants and shoes will have frequent contact with the board, rails and ground. Wear leather or canvas skate shoes with a rubber outsole for board control. Chino or denim stretch pants are popular for their durability and comfort. For the upper body, wear whatever keeps you comfortable, like a t-shirt or hoodie.