3. Biggie with the Versace shirt and glasses in "Hypnotize."
Versace has experienced a massive resurgence in hip-hop lately-but long before 2 Chainz was wearing Medusa insignia to the Grammys, there was this. Despite the dozens of ways rap has repped for the brand, no image persists more than this one. Biggie was living out his larger than life, mafioso raps right in front of our eyes.