How Kelly Killoren Bensimon Made the Hamptons her Home

How a modeling gig in the Hamptons turned Kelly Killoren Bensimon into a local.

Bensimon at a photo shoot in the Hamptons in 1984 at age 15

When Kelly Killoren Bensimon was growing up in Illinois, the far corners of Long Island were truly unknown territory. But when the highly motivated teenager moved to NYC at age 16 to embark on a modeling career, that changed. “I went out to the Hamptons for the first time for a modeling job and remember the drive from the city being so long,” recalls the tall brunette. “But then I looked out the window and I quickly realized why we were there.”

Her modeling ascent coincided with a particularly rollicking social scene out East marked by buzzy get-togethers at Calvin Klein’s compound and epic parties at producer Darren Star’s home. “These parties were so A-list that I was like, what am I doing here? They were a lot more exclusive back then, and there wasn’t social media to document it, so if you were invited, you didn’t say no. There was a lot more humility and pride.”

With Stephanie Seymour Brant at Bridgehampton Polo Club in 1997

Bensimon would frequently return out East to model. It was during one of those trips she sealed her destiny. “I was staying at the Maidstone Arms Hotel and I took a run down Further Lane. I thought to myself, one day I’ll have a house here.” Years later, fate delivered. She built a house on that very street, where she lived with her former husband, photographer Gilles Bensimon, and their two daughters, Sea and Thadeus.

Eventually Bensimon parlayed modeling into a writing career when she landed the position of fashion director at Hamptons. “People just think it’s full of rich people who don’t want anything to do with anyone, but it’s quite the opposite,” Bensimon says of the area. “I learned that there’s this unbelievable love and dichotomy of people who live harmoniously together.” Her experience out East also culminated in a book published by Assouline titled In the Spirit of the Hamptons.

Kelly Killoren Bensimon with her children, Teddy and Sea, in East Hampton in 2005

The East End was also the bucolic setting of her daughters’ childhood, where they learned how to bike, swim and surf. “Everything they know from their formative years is from being in the Hamptons,” she says. “The Hamptons is ultimately where I started my career and raised my kids.”