Years Active: 1996-2004
Key Members: Jay-Z, Damon Dash, Memphis Bleek, Beanie Sigel, Freeway, Kanye West, State Property
Elements of Style: All-black everything, Yankee hats, Rocawear, Freeway's beard
While Kanye West may get more credit for his impact on the fashion world, there's no denying Jay-Z's influence. From the first time you saw that Reasonable Doubt cover, you knew the guy in the fedora and the white scarf was about to takeover, so to speak.
By 1999, Jay-Z and his erstwhile partner Dame Dash dove into apparel with Rocawear, which is still a force to this day (although Jay rarely wears it himself). By 2003, Hov landed the first entertainer endorsement deal with Reebok and launched the S. Carter collection—predating 50 Cent, Rick Ross and Swizz Beatz getting in bed with the brand.
Around the time The Black Album came out, Jay opted to "Change Clothes." Smartening up for his new CEO gig, he left the jerseys alone and started rocking proper suits, button down shirts, and hard bottoms.
The Roc's influence on street fashion shouldn't be too surprising since they were of the streets themselves. Bleek did the doo-rag thing to perfection, and Freeway worked his beard into a personal signature. But it all begins and ends with Jay. He's the man who made the Yankee cap more famous than the team itself, and made his personal uniform all-black-everything way before the A$AP Mob. Today Jay-Z manages to balance his streetwear roots with an appreciation for dressing like a grown-ass man: whether rocking custom murdered-out Givenchy gear on stage, chilling with his wife on yacht in flip flops, or rubbing shoulders with the president in perfectly-tailored suits.