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1
The 50 Most Stylish Rappers of All Time

3. Slick Rick

Height of Style: "Children's Story" video
Signature Look: Assorted eyepatches, Justice scales on dookie gold rope chains, multiple rings, furry Kangols

Rick's truly original amplification of British Jamaican rudeboy style turned hip-hop on its ear with his Bally shoes, furry Kangols and cardigans draped in enough gold for an Ashanti King. Whereas Mr. T's layered jewelry came off as corny at times, Slick Rick's never looked out of place. It just worked. His influence is far-reaching—rappers as diverse as Tupac Shakur and Ghostface took meticulous notes. One style choice that no one else has been able to duplicate? His signature eyepatch.

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