Jessica Simpson | $200 Million

After performing in church choirs as a child, Jessica Simpson signed with Columbia Records at age 17 back in 1997. Her debut album Sweet Kisses sold two million copies in the United States, which saw commercial success with the single I Wanna Love You Forever. Simpson adopted a more mature image with her second album, Irresistible, and its title track became her second entry on top 20 of the Billboard Hot 100. It was also certified gold by the RIAA.

Aside from her musical pursuits, the singer launched The Jessica Simpson Collection, a fashion line of clothing and other items, in 2005. The brand has become an earner of more than $1 billion in revenue. Ten years after launching a footwear line with the Camuto Group, the singer-turned-mogul is at the helm of a fashion empire spanning over 31 product categories, which includes handbags, clothing, shoes, fragrances, jewelry, and home line—a wise investment planning, indeed.