Rocawear

The biggest money story in rap fashion. Jay-Z and Damon Dash, the founders of Roc-A-Fella Records, launched Rocawear in 1999, and by 2003 it was reportedly netting $700 million a year in sales through department stores like Macy's. In 2007 Jay-Z sold the brand's rights and intellectual property to Iconix Brand Group for $204 million, turning a merch-adjacent line into one of the best exits any artist has made from clothing. After that it ran largely as a licensed name, and the relationship soured into lawsuits before Jay-Z took the intellectual property back for $15 million in 2019. Read it as a business case study rather than a design label.