Ice Cube

Occupation: Rapper, Actor

Don't get it confused, his recent movie roles are a maturated million-dollar evolution for Ice Cube, but in his heyday as a member of militant rap group N.W.A., Ice Cube also influenced a generation with his monochromatic wardrobe. Crisp chinos, button-down flannels and black hoodies — his style was simple, Cali-gangster cool, but it made a statement. He also rocked throwback jerseys and snapback caps long before they were cool.