The 50 Greatest Fashion Moments in Rap Video History

12. Dr. Dre with the White Sox cap in "Deep Cover."

Year: 1992

The West Coast loved the black and white monochrome colors. Like Raiders hats, the White Sox cap was badass with no color to brighten up the mood and none of the glittery showmanship of the World Class Wrecking Cru. This was pure, grim gangster signification.

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