The afternoon I was scheduled to interview Kelly Killoren Bensimon over Zoom, the beloved, long-absent Real Housewives of New York iconoclast was running a couple hours late. As it turned out, she was attending the star-studded memorial service for her longtime agent Ivan Bart, the legendary fashion agent and former president of IMG Models, who died suddenly in early November at age 60. Despite her grief, Kelly didn't cancel our talk, and seemed especially contemplative.
"He was so incredible. Everyone was there," Kelly told HELLO! of the service, held at Spring Studios in Tribeca. "Michael Kors, Zac Posen, Brandon Maxwell, Chuck Bennett, Stephanie Seymour and I sat together, Carolyn Murphy, Lily Aldridge, Gigi Hadid, her mom Yolanda Hadid. Just a lot of big stars. I think that he would be very happy to feel the energy from everyone that loves him so much."
With Ivan at her side, Kelly, now 55, first entered the fashion world as a teen model; she later became editor of Elle Accessories, authored several books, and became an on-camera correspondent for Fashion Week events. By 2008, she was a 37-year-old divorced mom of two young girls when she was approached to join the cast of Bravo's Real Housewives of New York for season two; Ivan wasn't immediately sold on the gig.
"He was like, 'Are you sure you want to do this? I'm not sure this is something you should do.' And I was like, 'I've been behind the scenes for so long and nobody knows my name, it's time for me to spread my wings.' And he goes 'If this is what you want to do. I support you 100%.' And so we did that together."
Supermodel-gorgeous, outspoken and free-spirited-to-kooky, Kelly did indeed join the RHONY cast for seasons two through four, and became one of the most singular Housewives ever. She went viral before that was a thing, thanks to confrontations with Bethenny Frankel, a meltdown during an infamous cast trip to St. Barts (later dubbed Scary Island), and a nonchalant jog through midtown traffic. Over ten years later, Kelly has finally returned to the Bravo universe — and St. Barts! — via season four of Ultimate Girls' Trip: RHONY Legacy, joining her RHONY pals LuAnn de Lesseps, Sonja Morgan and Ramona Singer (plus Dorinda Medley and Kristen Taekman, who joined RHONY in post-Kelly seasons) for a wild vacation to the Caribbean. (Most of that same cast was initially assembled for a different, more extensive show concept simply called RHONY: Legacy, which was later scrapped under a shroud of unconfirmed gossip about salary negotiations. Meanwhile, season 14 of RHONY, with a completely new cast of women, aired earlier this year.)
In a long, free-ranging chat, Kelly told HELLO! about that decision to join RHONY, how she "packaged" Scary Island, the unidentified castmate who allegedly kept her off the air for 11 years, the recently recast RHONY, her life today, and more. This conversation has been edited and condensed for clarity.
Tell me how you were first approached to join RHONY.
When I was at Elle Accessories, I used to do these things for Tim Gunn at Parsons [School of Design]…they used to have all the senior students come and they would have people in the fashion industry judge the senior projects. I would sit there and talk them through everything. This later became Project Runway. They wanted me on another show to host. And the executive producer was like 'we're starting this new show [RHONY] and we really need to legitimize it, so can you come on? Ivan was like, 'You're editor of your second magazine. You've already written three books …you should take the hosting route." I was like, 'no, I think it would be fun to do something different..' I was young at the time. He was like "don't do it…don't do it."
Did you ever regret that you didn't follow his advice?
Bart was always such a pioneer and a champion of everything that all of the girls wanted to do. Reality TV, when I was on it, nobody really understood it; it really hadn't taken over yet. I don't regret going on the show. I don't regret it at all. I regret not showing more of my life and not being more open. I regret that. If I truly regretted the whole thing, I wouldn't have packaged Scary Island like I did for the media. I wouldn't have taken these iconic moments and tied a bow on them so that they could go fly into hyperspace and really make an impact.
I have so many follow-ups! What aspects of your life did you feel you did not share with viewers? You seemed an open book to me.
People didn't know about my career and assumed my money just fell off trees. I'm like, I've been working since I'm 15 years old. Really really working. I got a lot of slack for being a model. They're like, you just stand there and starve yourself. But you travel by yourself all over the world, meet new people every two or three days. Have to take care of your physical self, your mind. You have to keep yourself interested so that you don't burn out. I didn't know what I was doing, and it's not like I had a cell phone. It's not like I could text friends. I was writing people postcards all the time. It was a different time, and I was alone. I literally was raised by myself In this global world with different languages and different cultures and different values, and had to navigate that. I'm grateful that I was able to do that and still be the mother and human that I am today.
When you say that you "packaged" the Scary Island episodes, what do you mean?
We would get the episodes in advance before they aired. So when I saw it, I called my publicist and I said "We're going to take this to New York Magazine and I'm gonna handle it." So the reporter asked me "What was it like? I was like "It was Scary Island." She started laughing. She asked if I had a breakdown. I was like, it's "more of a breakthrough." So we had fun with it. And if there was a moment where my mental health or wellness was actually in question, I would never in a million years have packaged it that way. I would have brought doctors on. I mean, I'm an educated human. But I needed to take it to another level and have fun with that. You have to be a part of the conversation. Scary Island would never have been Scary Island today … but then we had no mental health awareness in 2008.
Right. The way Bethenny Frankel characterized it, she said she was concerned for your mental health at the time.
There are housewives that have their own narratives; that's their story and that's what they're gonna stick to. That's how they want to be perceived. I don't have a story. I just continue to reinvent myself and do the things that I love and do whatever I can to provide for my kids and just enjoy my life. If we can have fun doing it, that's even better.
In addition to Scary Island, another iconic moment was your argument back in the city with Bethenny, when you said "I'm up here, and you're down there."
It's so funny. People have used that over and over again. I've seen it absolutely everywhere. I told her, when we were in the scene, you're acting like a child and I actually work for a living and I have a lot of things going on. I have two young children. It's raining. It's Fashion Week. I've been trying to connect with you all day long because you needed your moment in the sun, your Joan Collins moment. You are a child, so you're gonna be down here. I am not Joan Collins, I'm gonna be up here, and I'm going to say, bye-bye. So I did.
What's your take on the all-new cast of RHONY?
I've known Jenna [Lyons] and Ubah [Hassan] for a long time. They're great and I loved watching them. The other women also did well, considering the big shoes they needed to fill.
What convinced you to finally return to the Housewives universe after all this time?
Luann's been trying to bring me back for 11 years, and I was never allowed to come back. There's a housewife that kind of put a block on me. I was not allowed to film, so Luann was always trying to get me back. Then, my daughter and I were in the Hamptons at a friend's birthday party, and I ran into Jimmy Fallon and his wife. Jimmy's like "You have to go back on Housewives! I'm gonna tell them because they've been asking me and they think that you're mad at Bravo" He's a good cheerleader. Then I got the call for RHONY Legacy and Luann called me, and she was like "You have to do this. It's gonna be so much fun." And I was like "Why not?" I thought we were gonna be filming for a longer period of time. And then we got the call for Ultimate Girls Trip. It came at a very pivotal point in my life where my youngest daughter moved out. I'm renting out my apartment. And so we were all having this big transition in our lives. You guys are gonna have a lot of fun watching me and how I navigate so much stress. That emoji where their head is exploding? That was me.
Wait. You said that someone was blocking you from returning to Bravo. Can you tell me who that was?
No, I can't. But there is someone that was blocking me. It's just so nice that people feel the need to impede your ability to make money. I would never do that. I've always been the one to bring as much money as I can to myself and other people. When someone is impeding your ability to make money and provide for yourself and for your family…
That's awful. So, before it was reduced to Ultimate Girls Trip, this series was meant to be a full, typical season of the show set in New York, RHONY Legacy. There's been a lot of chatter that castmembers couldn't get the salaries they wanted. What happened?
I don't really know what happened; people were talking about pricing; I'm not privy to those conversations. All I know is there were certain people that were invited and certain people that weren't, and that's all I know. I really don't get involved in that kind of stuff. That's not really my vibe. Some people like to micromanage the whole thing. I just like to hang out with my friends and have a good time and laugh and make sand angels. I honestly missed Jill Zarin. I really did. I miss Jill. I miss our relationship.
I think her superpower is her nurturing.
Any specific moments or incidents from Girls Trip you can tease us with?
Not yet! The most important thing is that the emotions and connections run deep and strong. Those rolling-your-eyeballs moments are not there, because these are real relationships. And I think it's going to resonate with a lot of people.
How was BravoCon?
Amazing. I've never been to a convention before, so I had no idea what to expect. I've only been to Vegas a couple of times — when I was promoting my cover for Playboy, for a birthday party where I gave free drinks out to everyone at the pool. So to go to Vegas meeting 30,000 Bravo fans and all the Bravo-lebrities, I was super nervous. There's all these fans screaming and yelling. We read on social media: You're too tall, you're too skinny. Your face, your hair, your nails, your teeth. You should have more kids. You don't have enough kids. it's always criticism. But it's so nice to be with fans. They're so excited. They know absolutely everything. I was almost crying on the panel. Almost lost it. I was so moved, and it was just really beautiful and remember, I haven't been on Housewives for 11 years.
Which Bravolebrities made the biggest impact on you?
James Kennedy from Vanderpump Rules: his mom and I met when I was 15 years old when I was shooting for Italian Vogue in Mauritius. She was there. And then [Real Housewives of Orange County's] Vicki Gunvalson, her ex-husband Donn was there. He's from the Midwest and he knew my parents. I met [Real Housewives of New Jersey's] Melissa Gorga and her husband on the plane and they're just the coolest. [Real Housewives of Beverly Hills'] Sutton Stracke! I'm obsessed with her. I love that she wears cat sweaters on dates. I definitely do that too. She's cute, she's fun. She's wild. She's feisty. And, like me, she's an equestrian, too. I was in awe of everybody. I felt so safe.
Outside of all things Bravo, what's a typical day for you? You're a real estate agent, you have a product line…
I make my bed, work out, take my dogs out and then I have a coffee and then I start rolling calls with my social media manager, my publicist. And my team at Douglas Elliman [Real Estate], we have our meetings; I work in New York, the Hamptons Palm Beach, Florida. I'm working on a property in St. Barts right now, a couple properties in Europe. So I don't have a typical day. I'm flying. I'm very excited about where I am in my life. I definitely want to write a new book about real estate and just enjoy, take every day as it comes. I don't have a five-year plan.
How are your daughters?
My oldest, Sea, graduated from Ole Miss, and she's a sports manager for United Entertainment Group. And then my youngest daughter, Teddy, who graduated from Trinity, she's a photo editor. They're both doing so great. Beautiful kids. They're both in the city, we're all five minutes away from each other. I'm so proud. I cannot believe I raised them on my own through everything that I've been through. I just put my head down. I was just like I don't care what anybody says, I will make money and provide for my girls so that they can have a better life than I had. That's all I wanted for them.
Almost forgot to ask: Ramona was originally supposed to be at BravoCon. Her appearance was then canceled, most likely because of a controversy in which she used a racial epithet repeatedly. Any comment?
It was so fun filming with her, and I think that everyone is going to love seeing the Ramona that they love so much on TV. And we had a great trip, and I can't wait for you to see us all on television.
Okay, I get it. You can't really comment. Thank you so much, Kelly!
I can't wait for you to see Trip. You're going to freak out—it is so hot. So sexy, so dramatic. They're gonna have to make an Ultimate Girls Trip handbook after that — the things you're supposed to do. Yell at your friends at dinner. Wear hot sexy clothes and drink way too much!
Get the lowdown on the biggest, hottest celebrity news, features and profiles coming out of the U.S. Sign up to our HELLO! Hollywood newsletterand get them delivered straight to your inbox.
