13. Tupac Shakur
Height of Style: All Eyez on Me era
Signature Look: Versace leathers, gold jewelry, bandanas
Pac remains the template for the fashion gangster: Overzealous tatt game mixed with high-end touches from labels like Versace. His bandana tied into rabbit ears struck mythic chords and remains one of hip-hop's most recognizable style flourishes to this day. A Dickies and Tims man to the fullest, his dedication to workwear was unwavering. Remember when he rolled up to the Grammys in a "Thug Life" beanie and coordinating Carharrt chore jacket, baggy jeans, and wheat Timberlands? Damn.