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The album sold over four million copies worldwide, and spawned the top three hit "I Wanna Love You Forever" (1999).
Hoping to achieve further success with her second album, Simpson adopted a more mature image for the release of Irresistible (2001).
In a July 2001 interview with Coventry Newspapers, Simpson explained "I recorded [Sweet Kisses] when I was seventeen years old and I'm twenty-one [this month] so there is four years of growth involved." Though the album's first week sales were nearly double that of her previous effort, Irresistible failed to match the success of her debut album; the record earned a gold certification from the RIAA for sales of 500,000 copies.
In This Skin debuted at number ten on the Billboard 200, selling 64,000 copies in its first week of release.
In February 2005, Simpson and Shinder launched the Dessert Treats edible cosmetics line, similar to their prior line but targeted towards a younger audience.
She also recorded the song "These Boots Are Made for Walkin'" (2005) for the film, which went on to become her fourth top twenty hit on the Billboard Hot 100.
Aside from her musical pursuits, she launched The Jessica Simpson Collection in 2005, a fashion line of clothing and other items.