In the words of Paul Varjak (“Breakfast at Tiffany’s”), “People do belong to each other.” Sometimes people belong to a town, more specifically, our town of Wilton. Anyone who’s ever had the privilege to know Dianne DeWitt or simply cross paths with her, knows that if anyone belongs to the town of Wilton and vice versa, it’s this former Ford model turned Berkshire Hathaway real estate agent.
Graceful, humble and Post-It-Note savvy (more on that later), DeWitt truly is the heart of hometown spirit, bringing her infectious enthusiasm to everything from the Woman’s Club Fashion Show to selling the sunset and river that runs through our town to the good people who ultimately portray (without putting a label on it) all that it means to be a Wiltonian.
Lesley Kirschner caught up with this could-have-been-a-Capote character (in all the best ways) for some hot spiced cider, warm words and thoughtful reflections on how to keep your ducks lined up, teaching your kids to be citizens of the world and why it’s okay for ColdPlay to make you cry.
1. Wilton is such an idyllic depiction of a small town with big heart. As someone who clearly portrays a whole lotta 06897 pride, what would you say are some of the main reasons young families considering Wilton as their zip code might choose here over other Fairfield County towns?
Dianne DeWitt: Wilton is a small town and its personality and character is completely different from every other town…and that can be said for any of these towns, they’d say the same thing, right? But we are still…the River Runs Through It. Our downtown is not one main street with lovely mom and pop shops or bigger national retailers on either side, as is a new town. We’re spread out and I think it’s also one of the reasons that folks really look at Wilton — because of our property. We have two acre zoning, except for those that are grandfathered in. So they see land and it’s just beautiful and it brings them privacy, which they may not have had if they were coming from, say, the city. It’s the landscape that I’m describing that brings people here to enjoy nature and then the community itself.
That’s what brought me here — the people, the feeling … that was 29 years ago. The people make the town, the people make the feeling, right? That’s why people come here, because we like to think of ourselves without putting a label on it, as “Wiltonians.” I think that the folks that come to visit here have to experience that for themselves. So many of them have friends here now and they’ve heard so many wonderful things … which are all true and when they visit, they can see and experience the town and the town of people.
What’s really fun is when they come back — our college graduates, our young people who go away and come back and want to settle somewhere; and because they had such a great childhood and a very friendly and positive environment. It’s surprising how many people come back — second and third generation … establishing businesses or starting families (if they decide to have a family) because they had such a great upbringing.
It doesn’t always work and so it’s a generalization. I’m sure there’s some people who say, “I’m very happy elsewhere,” but if they were here for even five to 10 years… it was an important part of their lives. Our public schools and our private schools around here are fantastic. There’s something for every child — theater, music, bands, art … of course the sports are amazing, right? But that’s what’s so nice … you can find one or two or three things and really immerse yourself as a student. My daughter had [former Wilton High School counselor] Dann Pompa and his door was always open and there was always an open ear.
I don’t have children in the school system right now, but from what I read and hear from my friends, there’s something for everyone and they’re encouraged to pursue it and [as parents], to follow the child’s gifts, talents and interests because we want them to be great citizens of the world. It’s not just about getting into ABC College.
Was that a challenge for you as a parent with your own kids? Making them a citizen of the world, making them responsible, making them accountable and helping them to be compassionate human beings? All of the stuff you can’t learn from a textbook or a chrome book…
DeWitt: We do our best … and, you have a community of friends too … personal friends, and your children have a community and it takes a village but it starts at home. What happens at school is a continuation. You want to have all of the children get along. Ideally. It doesn’t always happen in our world. We want everyone to respect each other. That’s the biggest thing, right? You don’t all have to agree but you have to respect each other — learn that gift early and respect what that person brings to the table. But also, it’s okay to agree to disagree. But yes, most of what you’re learning, the valuable learning is not coming from a textbook or a chrome book. It’s social and cultural and learning how to be around others and knowing how to collaborate respectfully.
2. You’ve spent many years in the spotlight looking stunning and camera ready. What would you say to young people who maybe feel a certain pressure to present or curate a persona? How do you stay healthy and balanced in the Meta verse?
DeWitt: Everyone has a story. I’m a college graduate with a music degree so I’m a singer. The background that I had was in professional performance, but in my modeling career I was always just me. I was always still myself. It must be very, very difficult [now] because it’s all artificial — looking a certain way. It’s so … prescriptive.
But I learned from my model friends. They were so unique, so beautiful in their own way; and that’s where my international appreciation came from and that’s what I want people to understand, whatever is your unique beauty (and I want young women in particular to understand this) — inner beauty, and given features … elements of themselves don’t necessarily need to be changed. I worked with a lot of models — Brazilian, Swedish, Moroccan, Italian, French, Indian — and I learned so much from them. The artificial elements, they’re all around us and it doesn’t mean that we have to succumb.
3. You’re gonna make me cry, Dianne. Okay, tell me about your work with the Wilton Women’s Club…I know you’re very involved with the fashion show…
DeWitt: I came to Wilton in 1997 and I slowly, surely was meeting women and making friends — mostly through our children, and I was going in and out of New York all the time. I really wanted to become more involved in the community with charitable causes. In 2002, I joined at the suggestion of some friends and we started this fashion show because the other fundraiser was the arts and crafts fair … huge undertaking, and it was wonderfully successful but then we needed to do something else and so the fashion show was born.
It’s had many iterations but that’s when it started, and it graduated to Rolling Hills Country Club. Sometimes we were even in a retail store doing it but it just grew and grew and grew and you know, it’s our big philanthropic fundraiser. We have a wonderful group and they continue to come back every year because they have so much fun.
The Woman’s Club is volunteer service-oriented and it’s grown over the years. We have a book club and a walking club and we volunteer for the seniors. We come together to prepare the meals for the seniors. We bake, we cook, we assemble and deliver to their homes. We also serve at Ogden House. When you give back, a little bit goes a long way. Everybody can do a little bit, right? And it comes full circle, whatever one can do comfortably, no matter what they’re going through … even if it’s just a little bit here and there — it helps.
I was also on the Philanthropy Committee and helped to select our beneficiary for 2026. It was very rewarding and I learned so much about all of the philanthropic organizations in consideration.
4. As parents (and moms especially), we bear the burden of emotional worry for our kids. What advice would you give to Wilton parents?
DeWitt: I’m a very organized person and if I’ve got my ducks in a row, I’m better at accomplishing things. I need to be organized.
Are you a Post-It Note girl?
Can I tell you, if I had invented Post-It Notes, I’d go buy an island somewhere. Yeah, but I’m creative. Physics was never in my cards. Math — I made it through. I’m all very much on that side of the brain. But both my mother and my father were very organized, so I think it was in my DNA. What’s so funny is that everybody uses their phones, which I do — my calendar is on my phone and people nowadays … these kids. However we organize ourselves with the phone, the computer … whatever, the idea is that you have your calendar there and so people say “then why do you need Post-It Notes?” Because I’m still a writer. I still write things down, yeah? And it’s right there. You don’t have to scroll through to find it.
I miss the days of just getting a flyer in the backpack. We’re bombarded across platforms — Schoology, Parent Square, PowerSchool, Instagram, Facebook…
I would agree with that. I’ll tell you this — when my daughter had soccer practice, we had to check Facebook and find out where we were playing … and now for literally everything you have to be on social media, on these apps. It’s a lot.
5. If someone wrote a book about you, what would the title be?
DeWitt: That Texas Girl … like “That Girl,” like Marlo Thomas, … but not that.
6. Is there a song that makes you cry without fail?
DeWitt: Yeah. Oh, my gosh, if I hear it … I have lines and songs. Oh, a gazillion, anything from Puccini. And also another one in the past four or five years is from Coldplay, “Something Just Like This.” Or I listen to Maria Callas and realize that sound is coming from her body … out of this world. I did a lot of operatic theater. I was more of a soloist but I went into theater — that’s why I came to New York.
7. Is there something you’ve recently realized you could do without in your life?
DeWitt: Less stuff.
You know, we often heard that from our parents, “Oh, you don’t need that.” And now I’m feeling it more than ever. What I always say is, whenever you’ve gone on a trip, say … a three day trip, and I take the clothes I need and two or three pairs of shoes … whatever … I take what I need. It fits in that hotel closet. It goes right back into my suitcase, and I never missed anything else. So if you could, if you could live like that, like you were living out of a suitcase, you know … subliminally, if you could say, I want to have a capsule of what I really need and then also what I really love…
Like Holly Golightly. But organized.
DeWitt: With Post-Notes. Pink Post-It-Notes. I love that.