Chris Bennett, 18, a senior at Glenn Hills High School.
Tommy Hilfiger shirt ($42) and Tommy Hilfiger baseball cap ($24), both from Rich's; leather pants ($200) from Wilson's; Air Jordan tennis shoes ($125) from Foot Action.
"This outfit is unique - it mixes casual with urban. ... I like to mix casual with urban, and it shows my individuality. I'll wear it to a game or a step show, or any event where there's a big crowd."