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1
The 50 Most Stylish Rappers of All Time

4. Big Daddy Kane

Height of Style: "Smooth Operator" video
Signature Look: High-top fades, gold chains, velour suits, four-finger rings

"A smooth operator operating correctly." Kane’s clean lines and the cameo with three cuts in his brow set the standard in the late ‘80s. Velour suits, four-finger rings, and the thick dookie chains—no one was doing it before him. Hands down, he was the most stylish member of the Juice Crew, defining the aesthetic of hip-hop's golden era.

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