Kelly Killoren Bensimon was born and raised in Rockford, Illinois, the daughter of well-to-do parents. Her father was a lawyer specializing in taxes and estate planning, her mom a teacher and licensed interior decorator. She went to a small private school, Keith Country Day School, where she ranked high in a class of 20 students, and where she excelled on the Rockford Marlins swimming team. Her specialty was the breast stroke. The Marlins made it to the tryouts of the Junior Olympics and she swam the relay in that competition.
Growing up, she loved children and imagined herself becoming a pediatric surgeon. But then, at 15, in Seventeen Magazine, she read about a contest. Elite Models was doing a nationwide search. Send in a photograph and a bio and fill out a form. You could win a trip to New York City and a possible modeling contract. This was to change her life.
“I finished second to Cindy Crawford,” she told me, “but Elite wanted both the winner and the runner up.”
Her parents encouraged her and the school said she could be away for the five days necessary. There was only one problem. As a sort of teenage rebellion, she had cut her hair short on one side while leaving it long on the other.
“I’d try to cover it up. I’d figure it out,” she told me. “Another thing was, I had a boyfriend at the time, but when I cut off my hair on one side, he said it was over. He wouldn’t see me anymore.”
Kelly flew to New York and stayed in an apartment provided by the agency with model Stefanie Seymour. At her initial interview with Elite, they told her they would be taking her out on “go sees,” where she would be presented, with photographs, to various magazine editors at Vogue, Cosmo, Elle, Glamour and others. She wound up doing a fashion shoot for Sante D’Orazio of Italian Vogue on this trip. Then she went home.
“What did your school mates think of all this?” I asked her.
“They were fine. Everybody was doing different things. They weren’t interested in what I was doing. It was a super-competitive school.”
Thus, at 16 began her modeling career. Soon she was sent to Ireland for a shoot. She became the Face of the fashion chain Ann Taylor.
Graduating high school, and knowing the importance of education, she went off to Trinity College in Hartford, Connecticut to begin the first year of what she expected would be a four-year college education. But it was an almost impossible schedule. She had all classes on Tuesday and Thursday. But on Monday, Wednesday and Friday, she commuted on the train back and forth from Connecticut to New York.
“I’d be on the 4:20 a.m. out of Hartford,” she said. “Then in the evening I’d be leaving Manhattan on the 6:10. This was too taxing. I felt like I wasn’t doing either well. I wanted to go to school full-time, and have a college experience. But it was now or never for modeling. So with my parents’ permission I moved to Paris and then to New York, with the promise that I would return to college at a future time. I wanted to be like my idol, Hemingway, and live like an American in Paris.”
Kelly was 18 years old. She lived in the 17th Arrondissement for a while, then moved to the 6th on the Left Bank. She modeled there, and enjoyed both Paris, New York and Milan, for nearly three years, then returned to Manhattan and enrolled in Columbia University. “I promised the Dean, if he’d give me a chance, I’d prove to him I could balance work and school. Columbia was the place that was going to give me the formula and tools I needed to move beyond modeling.
“I was so lucky to have parents who encouraged me to get an education,” she said. “I got my degree in English literature. In modeling, it was all about what I looked like. At Columbia, it was all about what I KNEW.”
Her favorite studies were Chaucer, Milton and Shakespeare.
During this time, she began writing for magazines. She was modeling about fashion and beauty. She could write about fashion. She also came out to the Hamptons, a place she had been to earlier in her career on modeling shoot, which she had never been able to forget. She recalled it very well.
“I had stayed at the Maidstone Arms Hotel for that shoot, which was at a small quaint hotel. I remember running down Further Lane. I thought, this is where I want to get married and raise kids.”
“That’s quite a thought,” I said.
“The houses were so beautiful, there were hedges, gardens, such an understated elegance. It was unlike any other place I’d ever been. I’d run down Dunemere Road to the beach, and the trees, the elms, they just lead you down there.”
On one trip to the Hamptons, when she had a house out here, she came upon a maple tree that had fallen, and she had its trunk cut, shellacked and made into the top of a coffee table with a glass top. She also began to study the history of this community—its natives, farmers, artist and writers, visitors.
At the age of 27, she married Gilles Bensimon, the International Creative Director of Elle magazine. She built a home on Further Lane in East Hampton, and was out here four days a week, in the city three. The marriage lasted 10 years. She has two children; Sea, now 15, and Teddy, now 13. A highlight of her life at this time was to be asked to give the commencement address at her high school in Illinois, and to speak to her Columbia University class about the Bikini Book she had published with Assouline.
In 2003, Kelly wrote a beautiful coffee table sized book called In the Spirit of the Hamptons. She had always loved photography, and has taken some pictures herself.
“There were incredible images in this book,” she told me. “I compiled images of Teddy Roosevelt at Montauk, Jackson Pollock, Franz Klein and all the German artists, art dealer Peggy Guggenheim. I learned about how the artists maintained their hierarchy. I call it ‘the towel hierarchy,’ for they had developed this for themselves on the beach. I also added photos of gondolas in Hook pond and beautiful scenes of the dunes and the sea, the fishing boats, the people.” This was all pre-Google, so it was challenging but exciting to compile all these diverse stories and
In the Spirit of the Hamptons, 10 years on, has been republished by Assouline and updated, with 90 new images and new text. This book has had sensational reviews.
Kelly also wrote a second beautiful book called American Style, about fashion, architecture and design from the turn of the century (the 20th), until now. More recently she wrote The Bikini Book and I Can Make You Hot!
She was asked to appear on the Real Housewives of New York for Bravo after the success ofher own show for Plum TV, Behind the Hedges, which was based on her column she had in Page Six magazine called the
“I was approached about co-hosting a fashion show with Tim Gunn, but the Bravo executives asked me to join Real Housewives of New York. It was only supposed to be for one season. But I was on for three seasons.”
Kelly seems to have mixed feelings about being on the Real Housewives of New York. One of the first filmed scenes resulted in having an altercation with another wife, Ramona Singer.
“I had taken her to the very special Richard Meier model museum, and she tried to ruin the scene. I was so embarrassed when we were filming, but she made a scene, and it aired.”
But Kelly stuck with it. “I’m from the mindset where you explore, celebrate and respect people, concepts, and things. But they saw me as the ‘Socialite/Supermodel’ and eventually, I guess because they needed a snobby socialite they wanted it to be me. I’m not a socialite; I’ve always worked all my life, but I’ll take supermodel. That’s a compliment.”
Her third year on the show completed, she retired. This past year, she sold the house she built on Further Lane. She now lives in SoHo, although she will be renting in the Hamptons for part of the summer. She can’t stay away. “New York is where I work, and the Hamptons is where I live.”
“What’s your day like?” I asked.
“I wake up at 6:30, drink a yogurt shake, workout, go running, or cycling. It’s illegal to run on the sidewalks. I’ve always run on the street.”
At the present time, Kelly is looking for a new challenge. After being a model, Editor of ELLE Accessories, columnist, author and TV personality, she’s ready for a change, and made one in January. In anticipation of it, she is getting an MBA from Northeastern University in International Business and Marketing. Maybe she will help designers with financing, or maybe she will continue to consult for brands as their “secret weapon.”
“I’ve always been excited by possibility. With the right tools, you can do anything. I have always believed in taking leaps of faith,” she said.
“What is that?”
“Putting myself in a modeling contest, going to school and working, moving to Europe, going back to school, and always welcoming challenges. I don’t like to look back. I just go for it. I’m lucky, for I know I can always go home.”
Kelly is involved a great deal with philanthropy, mostly where it helps children. And this is not something new. She has been involved with it since high school.
“When I was 16, I worked for the Red Cross. I helped with food drives. I was a fund-raiser. I seem to have a knack for raising money in unusual ways.”
Not long ago, she came up with an idea to raise funds for Hale House, an organization that helps disadvantaged children in Harlem. She created an event called “Get Your Jeans Off.”
I was in the Screen Actors Guild,” she said. “I went online and found out which actors were represented by whom. I contacted the agents and asked them to ask their artists/actors to use Sharpies to sign their denim jeans to auction them off. After I compiled Yoko Ono, Madonna, Michael Jordan, Julian Schnabel among others, I went to Peter Arnell and he created a catalogue of them, which won an art direction award. We then framed the jeans as art and sold them. That event raised over six figures, and created a database of over 4000 names.
Two years ago, Kelly took her oldest daughter to Haiti on a trip for Generosity Water. She works at Food Bank as one of their celebrity ambassadors in New York, packing boxes in the warehouses, serving food and stocking the pantries.
“Doing this work is a big part of our lives,” she says. She pauses. “I love working with my kids. And I feel everyone deserves an opportunity. That starts with a meal and clean water.”