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Simmons attended public school, but when she grew to 5-foot, 8-inches by the time she was ten years old, she became the easy target of schoolyard taunts and teasing. With no Asian population in her community, she also had difficulty fitting in with other African-American students who accused her of being white. Hoping to boost her confidence, Simmons's mother enrolled her daughter in a modeling class when she was eleven years old. Two years later, at the age of thirteen, Simmons was awarded an exclusive modeling contract with Chanel, and just after her fourteenth birthday, she boarded a plane for Paris to work under the tutelage of famed Chanel designer Karl Lagerfeld. Simmons quickly gained attention in the fashion world when Lagerfeld closed his haute-couture show with Simmons, who strutted down the runway decked out as a child bride. "Everything people thought was weird about me before," Simmons told People Weekly, "was now good."
For the next two seasons, while working with Lagerfeld, Simmons developed her taste for expensive luxury items and, despite her mother's advice, at the age of 15 had spent part of her small fortune on such purchases as designer bags, a Rolex watch, and a BMW convertible. "She always had the new Prada bag and would laugh at me because mine was from Wal-Mart," friend and Chanel roommate Tyra Banks told New York Magazine. Shuttling back and forth between Paris and St. Louis, Simmons managed, with the help of an academic coach, to graduate from St. Louis's Lutheran High School North on time.
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