Kelly’s first occupation in her professional life was modeling. Likewise, she began her modeling career during her teenage years. Kelly has also appeared in prominent publications such as ‘Elle,’ ‘Cosmopolitan,’ ‘Harper’s Bazaar,’ and ‘Gotham Magazine.’
In addition, she was the founding editor of Elle Accessories magazine, a position she held for only two issues before quitting. Kelly wrote several books, such as ‘In the Spirit of the Hamptons,’ ‘American Style,’ and ‘The Bikini Book.’ Likewise, she became a columnist for ‘Page Six Magazine’ with the publication of ‘The Socializer: Kelly Killoren Bensimon.’
Kelly was similarly appointed as a fashion columnist for ‘AM New York.’ In Miami, Florida, she also hosted the IMG fashion week and IMG swim show. In 2006, she became a spokesperson for Wool. She was designated an ambassador for Mercedes-Benz Fashion Week Spring 2007 the following year.
In 2010, Kelly appeared on the cover of ‘Playboy Magazine’. In addition, her ex-husband, Gillies Bensimon, captured these photographs. The following year, she appeared on the covers of ‘Shape’ and ‘Avenue magazines.
In 2012, she appeared on the cover of ‘New York Family magazine. Kelly gained notoriety after appearing in three seasons of ‘The Real Housewives of New York City.’ Similarly, she has launched several jewelry lines and written several novels.