Rachel's first job in fashion was at a Contempo Casuals clothing outlet in her hometown at age 14. After college, she came to New York City, where she worked as a stylist for magazines and music videos. She became an intern at the urban fashion line Rocawear, where she rose to become creative director of the women's and children's divisions and also met her future husband, Damon Dash. In 2005 she launched her own eponymous fashion collection.

In June 2008, Jones Apparel Group formed a joint venture with the Rachel Roy brand.

In August 2009, Roy launched The RACHEL Rachel Roy collection, an affordable diffusion line of sportswear, shoes and accessories. The label "RACHEL Rachel Roy" is available exclusively at Macy’s in the United States and at the Bay in Canada.

In summer 2009, Rachel Roy and Grammy-Award winning British pop-singer Estelle announced their collaboration on a jewelry line for the Spring 2010 RACHEL Rachel Roy collection via Roy’s Twitter feed. Roy designed a capsule collection in partnership with model Jessica Stam, for Macy’s stores and RachelRoy.com in Fall 2010.

The Rachel Roy collections are available at Saks Fifth Avenue, Bergdorf Goodman, Neiman Marcus, Shoewoo, and Nordstrom.

The World Liberty TV Fashion team was on hand for the debut of Rachel Roy Designs, at Lincoln Center’s Mercedes Benz Fashion week with honored guest Kim Kardashian in attendance.