Jockster means in slang: A physically fit individual who is trying to appear cooler in an urban setting. You are a mix of a hipster, a jock. A hipster who enjoys rock climbing, skateboarding, especially long boards and marijuana. You can also wear a polo or retro-t-shirt with ironic retro graphics, long hair, faux-hawks, or shaved head. Most often white males, untalented, educated at prep schools. (in Slang Dictionary, added by Kian Church)