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The 50 Most Stylish Rappers of All Time

18. Wiz Khalifa

Height of Style: Rolling Papers Tour
Signature Look: Chuck Taylors, tank tops, bleach spot

Like Snoop before him, Wiz Khalifa styles from behind a curtain of weed smoke and humorous bravado. The simplicity of his approach is exemplified by his full-bodied association with Chuck Taylors. He recently stunted on his album cover, but for the most part he keeps it understated in vests T-shirts and converse. His unfussy approach made him the spokesperson for the simple swag of the modern pothead, tying him to the west coast gangster chic and the new skateboard punk ethos at the same damn time. Wiz has recently changed up his style to channel a more '60s psychedelic rocker vibe. He's currently known for the streak of bleach running through his hair.

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