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1
The 50 Most Stylish Rappers of All Time

29. T.I.

Height of Style: Urban Legend
Signature Look: White tees, beanies, raw denim, suits by Ralph Lauren Purple Label

Tip made a smooth transition from hustler swag to CEO smooth. He had all guys thinking they could rock a tilted beanie just-so. Nowadays, he swings from his own Akoo clothing line to Ralph Lauren Purple Label suits. Tip's preppy lean gives him Hollyhood status despite his repeated visits to lockdown.

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