Although there was a huge boom in the late ’90s and Russell Simmons started Phat Farm in 1992, brands like X-Large and Naughty by Nature's Naughty Gear led the charge for clothing lines owned by rappers. Back then, most rappers with style rapped more about wearing clothes than peddling them. Guys like Biggie, Tupac, and Ghostface rapped about Versace, Armani, and Polo, not about how the Yeezys jumped over the Jumpman.

These days, it's assumed that any rapper that blows up and becomes a style icon eventually starts his own line—look at Lil Wayne's TRUKFIT and Kanye West's unreleased Pastelle line and polarizing womenswear collection.