When and where: 1997, Antonio Ansaldi ad

Antonio Ansaldi revolutionized custom gear back in the 90s. While Dapper Dan hooked the hip-hop world with Gucci and Louis customs, Ansaldi wanted to bring a new luxurious dynamic to a popular urban fixture: custom leather jerseys. By using rappers like Ma$e and The Lox to showcase what was he had to offer, the trend hit the ground running and created some of the awesome customs on this very list.