Created in 1999 by Roc-A-Fella Records co-founders Damon Dash and Jay-Z,Rocawear has annual sales of $700 million. Rocawear expanded its brand through licensing pacts to develop lines for children and juniors; socks and sandals; leather, suede, and fur outerwear; handbags and belts; lounge wear; big and tall; headwear; jewelry; and sunglasses; as well as co-branded product with Pro-Keds, State Property, and Team Roc.

On April 20th, 2007, allegations were made of raccoon-dog (tanuki) fur being used in two styles of jackets; Rocawear pulled all of the garments from the department stores where this product was shipped. A representative of Rocawear stated the company was unaware the fur was being used and had notified manufacturers it was not permitted. The items, in addition to being pulled from department stores, were also removed from the brand's official website.

R&B superstar Ciara has signed to be the new face of Rocawear.

In March 2007, Jay-Z sold the rights to the Rocawear brand to Iconix Brand Group for $204 million. Jay-Z will retain his stake in the company and will continue to oversee the marketing, licensing, and product development.

Shawn Corey Carter (born December 4, 1969), better known by his stage name Jay-Z, is an American rapper, songwriter, record producer, entrepreneur, and occasional actor. He is one of the most financially successful hip hop artists and entrepreneurs in America, having a net worth of over $450 million as of 2011.He has sold approximately 50 million albums worldwide, while receiving fourteen Grammy Awards for his musical work, and numerous additional nominations. He is consistently ranked as one of the greatest rappers of all-time. He was ranked #1 by MTV in their list of The Greatest MCs of All-Time in 2006. Two of his albums, Reasonable Doubt (1996) and The Blueprint (2001) are considered landmarks in the genre with both of them being ranked in Rolling Stone magazine's list of the 500 greatest albums of all time. Blender included the former on their 500 CDs You Must Own Before You Die.

Jay-Z co-owns the 40/40 Club, is part-owner of the NBA's Brooklyn Nets and is also the creator of the line Rocawear. He is the former CEO of Def Jam Recordings, one of the three founders of Roc-A-Fella Records, and the founder of Roc Nation. As an artist, he holds the record for most number one albums by a solo artist on the Billboard 200 with eleven. Jay-Z also has had four number ones on the Billboard Hot 100, one as lead artist.