Kelly Killoren Bensimon

50 Shades of Ingenuity

Kelly Killoren Bensimon epitomizes a new era of women on planet earth. Well educated, dynamic, smart and enterprising, she is daily proof of the burial of The Stepford Wife stereotype. Powered by inexhaustible energy, Kelly’s New York Frame of Mind transcends boundaries, limitations and negativity.

Ever since her teenage days when she began modeling, her all-out efforts won her coveted representations by Elite, Ford and IMG. She appeared in Spanish Vogue, Elle, Cosmopolitan, and Harper’s Bazaar Magazines while other significant achievements followed: she clinched the face of Clarins in a highly-competitive field, and proved that multiple layers of responsibility suited her genotype.

Kelly’s skill set flourished as she juggled full-time academics at Trinity College in Hartford Connecticut, Columbia University in NYC, and Northeastern University for her new adventure at NYU Stern’s Executive MBA. Each feat required oceans of discipline and precision time management. She was Editor-at-Large for Hamptons Magazine, and Fashion and Accessories Director for Gotham magazine. She became the Editor for Elle Accessories, and authored 7 books including anthologies such as In the Spirit of the Hamptons i,ii, American Style, and The Bikini Book. A portion of The Bikini Book’s profits was donated to New York’s Metropolitan Museum of Art. I Can Make You Hot was Kelly’s wellness book, and she was also a style columnist for The New York Post, AM New York, and guest editor for Avenue magazine.

Kelly hosted IMG Fashion Week, IMG Swim Show in Miami, and men’s wear events with GQ Magazine where she also modeled. Spring 2007 Mercedes-Benz Fashion Week in New York acquired Kelly’s ambassadorial talents and in 2009, Kelly joined Bravo’s The Real Housewives of New York City. In March 2010, she was on the cover of Playboy, and in September 2011, she scooped the cover of Shape. As if her schedule wasn’t full enough, she opened the NASDAQ at the New York Stock Exchange on September 1, 2011. In 2016, Kelly published a novel called A Dangerous Age based partially on her personal life. In it she exposes the art and publishing world via four female friends. In 2017, she launched The Second Course, which is a well-researched odyssey about the alluring food world.

Midwestern values are what have really helped me navigate my adult years, and reinvent myself. The solid foundation and suburban living encouraged me to dream big, and always seek possibilities

Kelly’s 1st line of jewelry was launched exclusively at Barney’s New York in 2007, and her second line at Bergdorf Goodman in 2010. At the time of going to press, she’d successfully launched her 7th jewelry line.

In 2019, Kelly joined Douglas Elliman Real Estate with the Holly Parker Team (#2 team) and in just two years, including a year of Covid-19, she broke the glass ceiling with multi-million-dollar sales. Her most recent sale was achieved on FaceTime during an international crisis.

I’ve saved the best till last. Kelly has been a dedicated single mom to two gorgeous daughters, Sea and Teddy, who are now launched – and off to College. She has set a powerfully resilient example to her girls on how to harness life’s opportunities.

And that’s one of the many reasons I proactively sought Kelly Killoren Bensimon for our Holiday cover. 2020 has been a calamitous year for the whole world, and yet, challenges energize Kelly – make her more creative. Her strong resolve to make lemonade out of lemons is contagious, and her positivity is a lifeline to people who are mired in fear. Kelly beautifully represents the words of Michael Bublé’s famous song – It’s a new dawn, it’s a new day, it’s a new life – and I’m feeling good. She’s that quintessential reminder of the hard-working characteristics that make America great.

Our sincere gratitude goes out to the team at IconicFocus Models NYC/LA. Together with Kelly’s innate creativity, the talent stream flowed in this joyfully Americana cover shoot.

Q: Your childhood in the mid-west formed the stable bedrock upon which you were able to flourish later in life. Describe that foundation.

KELLY: Midwestern values are what have really helped me navigate my adult years, and reinvent myself. The solid foundation and suburban living encouraged me to dream big, and always seek possibilities. Great parenting is also what makes for a resilient type of person. I was raised to do what I love and the money will come, to always try my best, and to show up. I’m so grateful to be raised during my formative years in Rockford, Illinois, and for my parents (my mother, who was the one of the first American Airlines stewardesses, and my father was an accomplished tax lawyer and estates planner). My parents put us first, and taught us everything so we’d never have fear, and would be up for everything.

Q: You were one of the few models represented by Elite, Ford, IMG, and now ICONIC FOCUS – who juggled full-time academics (at Trinity College in Hartford Connecticut, Columbia University in NYC, and Northeastern for your MBA, NYU Stern Executive MBA) with a modeling career and then, as a full-time single mom of two teenage girls. What advice would you give young girls today in terms of managing both schedules?

KELLY:: Education is so important, and formal education/college education is a necessity. It’s so easy now for anyone to get their education online. I’m humbled by the great mentors I still have, and by the incredible student body I was surrounded by. I learned so much from all of them, and it’s been amazing to work with one of my best friends from Columbia University in real estate, and my other good friend from Trinity College, who was in my freshman seminar, is my lawyer. I also think it is good for people to learn to compartmentalize. I wear a lot of hats, and have been successful in different fields for I compartmentalize what I need to do and prepare for deadlines. Being a model taught me a lot. I was always traveling all over the world, spent most of the time traveling alone, and worked with different people every other day – so I learned to manage expectations at a young age, and to be kind no matter what mood I am in. I also had a lot of respect for my agents who guided my career

Q: What were some of the special highlights during your modeling career including the countries you visited, the businesses you represented, and the people with whom you worked?

The Hamptons is a sanctuary for me. Bonkers and socialites live and work harmoniously together; the surf culture, equestrian culture, sailing culture, and I love how the most influential New Yorkers walk around in sweatpants and a paper

KELLY: My daughters love the Spanish Vogue feature and cover. I was the face of the Ann Taylor campaign at 18, worked for Vogue, Harpers Bazaar, Cosmopolitan, the face of Clarins, and ELLE magazine. I was on the 2010 cover of PLAYBOY and the 2011 cover of SHAPE. I was also a muse for Donna Karan’s DKNY collection, and had so much fun walking in runway shows for Mr. Valentino and Vivienne Westwood. One of my favorite trips was to Africa, where I learned about the Maasai tribe.

Q: You’ve also worked extensively in the magazine industry – including for Elle Magazine and Elle Accessories. What has that experience taught you – and what makes a publication a really great one? How do you contribute to that pursuit of excellence?

KELLY: I started writing for magazines because my professor, Alan Ziegler at Columbia University, encouraged me to start writing. I was literally one of the first bloggers for I worked for HAMPTONS magazine, GOTHAM magazine, AVENUE magazine, and started ELLE ACCESSORIES. One of the greatest takeaways for me was that I was asked to help sell the ‘book’ and edit the ‘book.’ When I started working for Hamptons in fashion and accessories, I literally called every designer and advertiser they had and asked how I could help them. I created my first column called In the Spirit of… which was a list of what I was moved by that week. I also created a column called MOST WANTED which was who wore it, why, where, and when. This forecasted my book AMERICAN STYLE. One of my favorite articles I wrote for ELLE MAGAZINE was called LA Confidential where I highlighted the most chic designers, artists, and beauty and fragrance designers from LA. It was important for me to showcase the incredible talent that comes out of LA. For me, a great magazine is one that resonates. You have to know your audience, appreciate the reader, and clue them into that which they don’t have access. It’s hard to be cutting edge with information, but it’s also exciting to be a hunter and gatherer for the most discerning readers.

Q: Your natural artistic abilities combined with your intensive research capabilities made you the ideal author for the book, “American Style” – which you wrote for New York’s Metropolitan Museum. During that time you collaborated with Vogue’s Editor-in-Chief, Anna Wintour. Describe that fascinating experience, and how much you enjoyed working with Anna.

KELLY: I have written 4 anthologies for Assouline publishing. I created the series: In the Spirit of… and started with In the Spirit of the Hamptons i,ii. Writing American Style for the Costume Institute at the Metropolitan Museum Of Art was a game changer for me. Anna Wintour gave me full access to the VOGUE AND CONDE NAST archives. It was an honor to be given that kind of free reign with her most revered collection. It was also incredible to be asked to be a part of the Costume Institute – which is invitation only. I feel so humbled that she gave me so much freedom with her archives. I have a lot of respect for women in business and especially for women who are pioneers and game changers and who add greatness to society. Anna is a unique and evocative woman. I was given a lot of responsibility and I’ll never forget that opportunity. Bergdorf Goodman asked me to feature the images from American Style on heir windows during New York Fashion Week, and I was immediately asked to create ELLE ACCESSORIES. There was one period of my publishing career where I was working for all three magazines at the same time. I’m a big social history buff, and I have a lot of respect for who people are, and how they live.

Q: You juggle a myriad of professional pursuits including commercial and residential Luxury Real Estate selling with Douglas Elliman’s Holly Parker Team – the #2 team at ELLIMAN, a jewelry business of 7 collections of jewelry, 3 seasons of an outerwear line with Pologeorgis called Enville (French for ‘in town’). Describe how your pursuits complement each other, and how you are able to juggle all of them at the same time?

KELLY:: I haven’t done that much. I’m just very good at compartmentalizing. My 7 jewelry lines came out of a love for making personalized jewelry for my friends on modeling shoots. It was first sold at Barneys New York, Bergdorf Goodman, Bloomingdales, and then on HSN. I consider myself a good synthesizer of what I love. All of my jewelry came from what I love and it helped that I was the Editor of ELLE ACCESSORIES and exposed to the most beautiful jewelry in the world. My outerwear collection came from growing up in the Midwest and always recognizing the importance of a great-looking winter coat. I’ve learned about fashion and style from the masters of the universe. And I wear clothing with an effortless style. I’m known for my bohemian yet feminine sense of style. Nothing I wear looks complicated but it’s always good quality – and that speaks volumes. I have also used my social media as a way to promote what I love. I’m not an influencer in the sense that I’ve been doing this all my life. I just didn’t have social media growing up. I feel that being a reality star is a great way to clue the viewers into how things are made, and why I like them. Trust is paramount. Real estate was a natural progression as I oversaw the building of my Further Lane house. I also sold that house and realized I wanted to go into real estate and show how respectful I am of the transaction, but also respectful of those who are buying and selling their biggest asset. My first month of working with the Holly Parker Team, I sold an apartment for almost $8 million, and my portfolio is close to $70 million. I sold another exclusive apartment in Brooklyn over FaceTime during COVID-19. Everyone has a brand, and everyone can do whatever they want; they just need to be strategic and work smartly – not necessarily harder.

I wear a lot of hats, and have been successful in different fields for I compartmentalize what I need to do and prepare for deadlines

Q: And yet, there’s more to being successful in business.

KELLY: Being successful in business requires Adapting, Surviving and Thriving. We already talked about how my father always told me to do what I love and the money will come. But you also have to resonate with clients. I think the reason I resonate with clients is because of my authenticity, and my education, and strategic partnerships. In all of my businesses, I work with strategic partners. I believe in one more than zero. No sale isn’t ok. One sale means more sales. I also do what I say I’m going to do – this is really important. When people talk about me in business, they use the word ‘trust’ a lot. I never over promise or under deliver. I just make it happen.

Q: You are affectionately called the “Tastemaker” by the NEW YORK TIMES. How did that name evolve in terms of all your passions and interests coming together?

KELLY:: Ironically enough, years before I worked in real estate, I was the image for a building on Beekman Place. My value ad was my list of the best of the best to make your 5-million-dollar apartment have a 5-million-dollar lifestyle. Where do you get the best flowers (not the most expensive, but the best)? It was a natural progression for me to work with the Holly Parker Team at Douglas Elliman for they represent some of the most exquisite properties in both the Hamptons and New York City. Those are the two markets, including Florida, where I work.

Q: Your two daughters have been your priority this past 20 years. Your youngest, Teddy, has just gone off to Trinity College – your alma mater, and Sea is a senior at Ole Miss. Explain your parenting formula and how it has worked so well for your family? The proof is in the young adults you’ve launched.

KELLY: Thank you for that compliment. It’s not easy raising children alone and I salute every single parent! I make sure my children realize I am the adult – and I am always talking about recognizing problems and creating solutions. We are not a family of complainers – but a family of doers. The girls and I have worked with FoodBank4NYC for over 11 years: we have served the homeless, danced with the seniors, decorated the Foodbank pantry during holidays, worked in the pantry with the families, packed boxes in the warehouse, and even made chocolate chip cookies. We have beautiful memories helping our New Yorkers.

I have also worked with Madison Square Gardens “Garden of Dreams” for the past 5 years, and have had the wonderful opportunity to see children with disabilities enjoy their senior prom, and perform in a talent show. I feel so grateful to work with such beautiful children who endure so much hardship on a daily basis. Both are powerful events to be privy to.

My oldest daughter, Sea, and I have worked with “Generosity Water”, and funded 3 clean water wells in Port-au-Prince, Haiti. It’s been an eye-opening experience to work with the Haitians, and an honor to bring them water. There are no words when you see families smiling and with buckets of clean water; we can never take that for granted. Water fuels opportunity.

This past October 1, I organized a NYCEAN event for New Yorkers to be proactive about cleaning up our city. I was so ashamed of how our city had been treated during Covid-19, so I enlisted New Yorkers to get a garbage bag and fill them on October 1, 2020 from sunrise to sunset.

Q: Your philosophy on life; Fitness, Health; Multi tasking.

KELLY: Every day is a new day. I am blessed with a positive mindset. I have endured a lot of hardships – yet have always made the best of every situation. The more you put yourself out there in life – the more you set yourself up for scrutiny. I’m not the skinniest, the youngest, the fittest or the prettiest woman, but I am proud of who I am. I work out every day to keep myself on track. I’m fortunate enough to ride horses with John Whittenborn at Two Trees Stables in the Hamptons, and I’m smart enough to put my safety belt on first. Take care of you, and then take care of others. I believe in personal empowerment and self-respect.

The more you put yourself out there in life – the more you set yourself up for scrutiny. I’m not the skinniest, the youngest, the fittest or the prettiest woman, but I am proud of who I am

Q: What are your favorite sports activities and relaxation passions?

KELLY: Riding horses when I can. Sometimes, I’ll take my dog, Fluffy, and drive to the Hamptons. I’ll ride, and have lunch with my friends. I just try to do something every day that makes me happy. It keeps me on track. My friends are really important to me.

Q: Our Cover Shoot epitomizes who you are. How would you define that?

KELLY:: I really enjoyed shooting this story for you. Matt Albiani, the photographer, is one of my oldest friends and it shows that I feel at my best around him: relaxed, calm, easy – that’s who I am at the core. I’m a home body who loves her solid friend group.

Q: You love The Hamptons.

KELLY: It’s a sanctuary for me. I remember running down Further Lane one morning before a shoot, and thinking to myself, “One day I will have a home here.” It has tradition. Bonkers and socialites live and work harmoniously together; the surf culture, equestrian culture, sailing culture, and I love how the most influential New Yorkers walk around in sweatpants and a paper. It’s a relaxed vacation destination where people have historically taken time with friends and family. Some of my best friends are from the Hamptons.

Q: What has life taught you?

KELLY: To be kind. I’ve raised my children with the ideology that everyone has a story, and to allow each individual to tell their story and to listen. I am constantly working on being more kind and a better listener. You don’t have to win in life. You just need to do the best you can do. Bring others with you. And, always be better and kind. I want my tombstone to read: “she was a great mother and friend”.

Q: One good thing that came out of our Covid-19 year?

KELLY: I got to spend several months with my college-aged daughters. I’ll never have that time again in my life. I’m grateful for every second we spent.

Q: What aspect about being on ‘Housewives of New York’ are you grateful for?

KELLY: The opportunity for people all over the world to see me. You can’t be fearful of how you are going to be perceived, You just have to enjoy the process. I made two great friends out of it, and I made a lot of new friends because of it. I would never have the career I have right now, and wouldn’t be able to provide for my daughters without the show. I’m grateful for every aspect of that time of my life.

Q: When you treat yourself, what is your favorite food?

KELLY:: I LOVE chicken wings and beer!

Q: Favorite movie and favorite book?

KELLY: My favorite movie is “It’s a Wonderful Life”. I love “The Gift of the Magi” and “The Things They Carried” by Tim O’Brien.

Q: What activities bring out the ‘fun’ Kelly?

KELLY: I am always FUN! I have a ton of energy and I love to have a good time. Honestly, no activities bring out the fun in me; it’s the friends I surround myself with.

Q: You didn’t wear any makeup on your skin for the cover shoot. How do you maintain a healthy glow?

KELLY: I’ve always been scared of using products on my skin for I had really bad acne the entire time I was a model. I started using Dr. Dennis Gross’s products and am getting bi-monthly hydrating facials at his Hamptons and New York practice. My skin has this healthy, natural glow. I joke with my friends and say, “if you know you glow”.

Q: An indulgence you particularly enjoy?

KELLY: I love to watch reality TV and hang out with my dog Fluffy and eat coconut chips, and ski “First Tracks” with my girls in Aspen, Colorado.

Q: How will you spend the Holidays this year-end?

KELLY: I always spend the holidays with my family in South Carolina. I love being with my father and my twin brother and his incredible family. It’s my favorite time of year.

Q: Your wish for 2021?

KELLY:: I wish for a calmer and healthier world. And, I hope that anyone who has endured hardship during this time reaches out to friends and family for help. We are all in this together: one world.