Kelly Jean Killoren was born in Rockford, Illinois. She began working as a model while in her teens.
Kelly graduated from Keith Country Day School, a college prep academy in Rockford, Illinois before attending college. She attended Trinity College, Connecticut, but left after a year. She graduated in 1998 from Columbia's School of General Studies for non-traditional students, with a degree in Literature and Writing. She completed an MBA with a focus on International Marketing at Northeastern University in 2015.
As a model, she appeared in magazines such as Elle, Cosmopolitan, and Harper's Bazaar, and she was once the face of Clarins. She appeared on the cover and in a six-page pictorial in the March 2010 edition of Playboy, which was photographed by her ex-husband Gilles Bensimon. In September 2011, Killoren Bensimon was on the cover of Shape and was featured in a pictorial based on her exercise routine.

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