Kelly Bensimon Bio
Kelly Bensimon is an American Actress, glamour model, designer, and businesswoman. Born Kelly Jean Killoren on May 1, 1968, in Rockford, Illinois, she has also been credited as Kelly Jean Killoren Bensimon. She appeared in Playboy in March 2010 at 41, adding the feature to her public career. Her appearance came during Playboy's contemporary era of international and digital publishing.
Bensimon has natural breasts, brown eyes and brown hair. Her measurements are 34-24-36.
Kelly Bensimon brings a polished New York glamour to the Playboy frame — tall, athletic, camera-aware, and shaped by a life lived between fashion, television, publishing, and business. Her beauty has always carried a certain East Coast sharpness: elegant but not fragile, sophisticated but never cold, with the confidence of a woman who understands how to move through society, media, and the lens without losing her own sense of control.
Before her Playboy moment, Kelly had already built a recognizable public identity as a model, author, editor, designer, and television personality. She became widely known as a full-time cast member on Bravo’s The Real Housewives of New York City from seasons two through four, where her mix of glamour, lifestyle, and strong personality made her one of the show’s most memorable figures. She was not simply a reality-TV presence; she was a woman with fashion-world history, editorial instincts, and a name that already belonged to New York’s social landscape.
In March 2010, Kelly Bensimon appeared on the cover of Playboy and inside the magazine in a six-page pictorial photographed by her ex-husband, legendary fashion photographer Gilles Bensimon. That detail gave the shoot a more intimate, fashion-driven charge. Rather than feeling like a standard celebrity pictorial, the images carried the confidence of a woman being seen by someone who understood her history, angles, and public mythology. At that moment, Kelly brought Playboy a more mature and self-possessed kind of allure — glamour with experience behind it.
Her career has always moved beyond modeling alone. Kelly has written multiple books, including The Bikini Book, In the Spirit of the Hamptons, and American Style, each reflecting her interest in fashion, lifestyle, beauty, and culture. In September 2011, she appeared on the cover of Shape and was featured in a pictorial centered on her exercise routine, reinforcing the athletic discipline and body confidence that had long been part of her public image.
What makes Kelly memorable is the way she blends glamour with enterprise. She has been a model, actress, designer, author, businesswoman, television personality, and lifestyle figure — a woman who turned visibility into a platform and style into a career. Kelly Bensimon’s Playboy appearance belongs to that larger story: not a sudden reinvention, but another chapter in the life of a woman who understood that confidence, beauty, ambition, and self-possession can be their own kind of power.
