COVERSTORY  12.24

Dee Hilfiger

Quality of Life

Iconicfocus Models NYC/LA
Fadil Berisha Photography
Story by Diana Addison Lyle

When two uniquely special people find each other across the world and discover that their values are in sync, something powerful happens: a love story germinates and flourishes so profoundly that the whole becomes much greater than the sum of the parts. Dee Ocleppo and Tommy Hilfiger met in Saint-Tropez in 2005 and built a relationship that amplified their core traits. When their hearts merged, they began the best chapter of their lives, and the fruits of that are evident in their family life and in their soaring careers.

From the inception of this cover story, Dee’s proficiencies and passions shone. Photographic maestro Fadil Berisha and Dee fed off each other’s sense of style and expansive vision. The photographic day flashed by with imaginative ideas and infinite creative flair. It was dynamically energizing and a reminder of how much the human spirit thrives on art, beauty and flavor. Our interview took place the morning after Dee and Tommy flew back to Palm Beach from Mustique, a private island in Saint Vincent and the Grenadines, where they had decompressed and exhaled. Dee expressed why they love the island so much:

“Tommy has had the Mustique home for over 30 years, and we go there often because of its beauty and serenity. I love swimming in the water there. Our house is indoor/outdoor so there’s always this feeling of openness and fresh air. The place forces you to slow down and completely relax. It’s uncommercialized with zero entertainment, so you disconnect and recharge in nature. Everybody knows each other on the island, and homeowners have to be approved by a Board to purchase a place there. It feels like a big, happy family.”

Dee was born in Cleveland, Ohio to immigrant parents: a radiologist father and a microbiologist mother and then the family moved to Rhode Island where Dee’s formative years occurred.

“I was very aware of my parents being different and when you are young, you want to conform and fit in,” she explains matter-of-factly. “Mom was British and Dad was Turkish so they both spoke with their respective accents. As I got older, I realized that being different was a superpower but as a child, I didn’t appreciate it, probably because I knew that children can be cruel towards outsiders. I was very shy, and I wanted to shield myself from bullies.”

I wonder at what point Dee was aware that she was enormously creative.

“I don’t recall thinking of myself as being very creative. However, now that I think about it, I do remember winning a contest in elementary school where we painted designs of columns. I think I had a definitive sense of what appealed to my eye, and that seems to have served me well.”

Dee’s style is undeniably elegant, and her fashion sense was probably polished when she was a child. Her mom brought home fashion magazines and she pored over Vogue and Bazaar in the late 1960s and 1970s.

“I was hugely inspired by fashion and glamor, and it extended to beautiful homes and environments that I thought were captivating. Those thoughts became dreams of what I wanted my life and my environment to look like when I became older. My bedroom at home was always immaculate and organized. I said to Tommy how amazing it is that those organizational traits were so evident at age 6 and they’ve stayed with me to this day. I’m a neat freak!”

Dee’s launch into fashion modeling in her early 20s was a juxtaposition to her life in Rhode Island.

Tommy and Dee Hilfiger

When Tommy met Andy Warhol, he loved how he took popular culture and turned it into art. Tommy has certainly taken a page out of that with his Hilfiger brand. Just like Warhol, he loves to include celebrities, athletes and musicians into his designs

“I attended an all-girls Quaker School. From there, I went to Southern Methodist University and so I had led a very insulated life. When I started modeling, an entirely new world opened to me. I was exposed to very different people in multiple countries. Some were lovely and invigoratingly creative, and some were exploitative. That was a rude awakening for me. Fortunately, I was in my 20s when I went off to Paris, so I was less vulnerable than the 14-year-old models, but I certainly encountered some nefarious people along the way and that was a moment of reckoning and a definitive growth spurt for me.”

We fast-forward to 2005 when Dee was newly divorced from an Italian tennis player and living in Monte Carlo with two young children. The Cannes Film Festival was taking place nearby and the serendipitous meeting with Tommy Hilfiger took place in Saint-Tropez.

“I didn’t know a lot about Tommy when I met him,” Dee remembers, “and my first assumption was that he may have been gay because statistically, I hadn’t met a lot of straight fashion designers. He wasn’t on my radar, but once I started talking to him, I discovered what an absolutely lovely human being he was. He was such a kind man and through our conversations we uncovered that we each had a special needs child – and both were on the autistic spectrum. That deep understanding sparked a profound friendship. Tommy is like the Fred Rogers of the fashion business, and I was enormously drawn to that. Then I discovered that he wasn’t gay and that was the beginning of our love story. Our very strong friendship base served us well and I’m a great believer in the value of a relationship building from the solidity of a trusted friendship.”

When the Hilfigers married, they were bringing together six children, and then they had their seventh child. Integrating a family successfully has its challenges – especially when three of their seven children have special needs.

“Patience is the number one necessity,” says Dee. “It’s not always easy being a stepmother to four children. Understanding our children’s needs is vitally important, as is possessing huge measures of compassion. I think we make it work with tons of love and determination. Commitment, consistency, work and determination all play into it.”

Given the Hilfigers’ experience with children on the autism spectrum, I ask Dee if she thinks that substantial headway is being made in understanding autism.

“I’m hopeful that with AI (Artificial Intelligence), maybe we can make significant headway with autism research. My hope is that it can help us integrate all the neurological research that’s being done in so many sectors, including Alzheimer’s. One of the issues with autism is that it’s such a broad arena. There’s that expression that if you meet one child with autism, you’ve met only one child. The brain is such a complex organ, and we need to invest more in the research. While I’m not a doctor or scientist, what concerns me is that we are being told that autism is 40-80% likely caused by a genetic mutation. However, there is no history of that genetic mutation in my family. I’d like to truly understand what causes the genetic mutation and if there are environmental factors contributing. Some people feel that autism isn’t something that needs to be fixed, but that depends on how severe it is. One of my best friends has a son who is unable to speak. My kids have it less severely and they are wonderful people, but I would like to understand the germination of autism.”

Dee’s entrepreneurial career in fashion designing started in 2011 when she founded Dee Ocleppo, a line of affordable luxury goods. The objective was to fill a gap in the market by offering luxurious items, such as artisan-made shoes, with silk scarves, pajamas and cashmere. She describes the inception.

“Tommy had been talking about a collection he was doing, and I had this idea for a bag, and he casually said, ‘why don’t you do it?’ I showed my prototypes to the head of HSN, Mindy Grossman, and she loved them. From there I went on to become Creative Director of Judith Leiber, and we expanded to shoes, home and jewelry.”

We go to Mustique often because of its beauty and serenity. I love swimming in the water there. Our house is indoor/outdoor so there’s always this feeling of openness and fresh air. The place forces you to slow down and completely relax

“I’m about to launch a new line with home and home accessories with QVC called Mrs H. It started with one item, and it’s grown exponentially through the years.” Mrs H becomes available to the public on November 26th, 2024.”

When creativity is driven by passion, it never feels like work, and that’s an accurate assessment of Dee’s immersion in her productive lifestyle.

Our cover story photoshoot took place at the Hilfigers’ gorgeous Palm Beach residence. It’s an oasis of beauty and Dee describes what she most wanted to achieve in the home.

“I love the greenery in Palm Beach. I also love the happiness in our home that is promoted by there being so much light. Our outdoors meld with our indoors, and it is bright and colorful. We sold our Greenwich and Miami homes to purchase this home and we consolidated what we loved about our former homes into this Palm Beach house. It has everything that we love. We have a lake at the back and an ocean in the front. Being surrounded by water is something we so appreciate.”

I remind Dee of the fact that when she was choosing colleges after graduating from high school, Pepperdine University was heavily on her radar. Did Pepperdine’s stupendous view of the Pacific Ocean have something to do with it?

She laughs, “Yes, I’ve always been obsessed by water. When we were in Mustique this week, I was literally always in the water. I admit to being a little bit timid here in Palm Beach because of the prolific number of sharks. While I respect them, I don’t particularly want to encounter them.”

The Hilfigers’ art collection is striking – from the Picasso above the fireplace – to a prolific Andy Warhol collection.

“We’ve bought and sold art like we’ve bought and sold homes,” Dee explains. “It’s something we are passionate about and it’s fun. Tommy is very drawn to Andy Warhol and as you can see, we have two Warhols in our entrance. Tommy met Andy in the early 80s and he loved how he took popular culture and turned it into art. Tommy has certainly taken a page out of that with his Hilfiger brand. Just like Warhol, he loves to include celebrities and musicians into his designs. He’s always loved sport, entertainment and music and he’s taken celebrities from all those areas to partake in his campaigns. He gains inspiration from them, and it ignites his imagination. Understanding popular culture and how it constantly changes is important. With technology and streaming, it can become overwhelming with the sheer volume of instantly accessible information, but Tommy and I try to keep up with it all. He’s better at it than I am. He’ll know the name and details of an elusive rapper, and it always impresses me how much he keeps up with it. We both make a concerted effort to be informed on who is trending and this also helps us to understand our consumers.”

The Hilfigers give back to society in spades with breast cancer, AIDS and autism amongst their greatest contributions. Dee supplies the specifics:

I believe 1000% that gratitude is the magical sauce to life. It’s such a simple concept but it’s powerfully effective. It’s too easy to complain and doing that becomes habitual. I’ve always walked through life with gratitude

“We’ve had a long partnership with the Lauders, and we’ve been big supporters of BCF (Breast Cancer Foundation). Those are the high-profile charities that we support, but we do many more that are under the radar. I’m on the Board of GLAM4GOOD, for instance. Tommy and I are very aligned with a lot of our thinking. We both feel incredibly fortunate that for whatever reason, God put us together and we found each other. When you are as blessed as we have been, we feel obligated to help others. We do assist a lot of people including family members, and it comes from a place of genuine compassion.”

Dee shares how her family will be spending the Holiday season.

“For Christmas, one of our traditions when the kids were young was to get these prefabbed gingerbread houses but as the kids get older, our traditions are changing. Tommy’s eldest daughter, Ally, now has a child, so the next generation will reinvigorate the gingerbread house-making tradition. We’ve also found that as our kids become young adults, it’s harder to get everyone together at the Holidays, but we certainly try. We celebrate on the morning of Christmas with gift opening. Our traditional turkey dinner is around 3 pm. We love turkey for Thanksgiving and Christmas. My son, Sebastian, can eat turkey every day. That’s his favorite meal. Tommy and I travel a lot, particularly to Europe, but we do always try to be home for Thanksgiving. I love the tradition with all the accoutrements, and we love to watch football! That’s the ideal Thanksgiving. Because I grew up in Rhode Island, I’m definitely partial towards the New England Patriots, especially when Tom Brady was there. We are also friends with Robert Kraft, so we’re big Patriots supporters.”

Learning about the Hilfigers’ favorite places in the world offers us a vicarious immersion into some of Europe’s beauty:

“We love Italy,” Dee enthuses, “particularly Venice. It transports me in a time machine back to another era. We also love to ski. We used to take our kids to Courchevel. I’ve lived in Europe most of my adult life, firstly as a model in Paris and then I lived in Monte Carlo during my first marriage. What I’ve always appreciated about Monte Carlo is the mild climate, its safety, and it is surrounded by water. It’s also so accessible to other parts of Europe. From Carlo you can drive to Rome, Paris, London or Milan easily. I loved that instant access to so many different places. I also love Greece in the summer, the water, the food and the people.”

Dee’s priorities are crystal clear:

“My top priority is to raise good, happy children who are strong, smart, kind, and independent. That’s no small undertaking. While we have more access to professional resources and more information, the fundamentals of raising children are the same even though the semantics vary.”

Another vital and central component to Dee’s quality of life is gratitude.

“I believe 1000% that gratitude is the magical sauce to life. It’s such a simple concept but it’s powerfully effective. It’s too easy to complain and doing that becomes habitual. When I was young, even though I had much less then, I was always grateful for a roof over my family’s head, and access to fundamental necessities. I’ve always walked through life with gratitude.”

On a broader note, she says,

“Our children are being raised with a lot more than Tommy and I ever had, and we make it a point to challenge them if we see any signs of entitlement – even though it’s a tough arena to navigate. I started working when I was 13 years old; I was babysitting and cutting the grass. It’s so important to have our children understand the importance of getting a job at an early age. That way they begin to respect money because they realize what it feels like to earn something. There’s pride in earning. My son recently asked me for some extra money, and I told him ‘No’ and I explained why. I told him that for his own sake and for his future quality of life, he has to learn to figure it out and he has enough resources to problem solve. I also pointed out that I’m not always going to be around. I thought he might hate me for drawing that line but in fact, he ended up thanking me.”

I’m about to launch a new line with home and home accessories with QVC called Mrs H. It started with one item, and it’s grown exponentially through the years

I ask Dee to imagine that it’s her birthday. What meal would she most enjoy?

“I love Indian food. I’m definitely a spicy girl, and since I don’t get to eat it often, that would be a treat on my birthday. I also love Italian food. Pizza is one of my favorite foods of all time.”

When it comes to complete relaxation activities, she describes her favorite down-time indulgences:

“I like to get into a Netflix show and that’s a decadence: to binge watch something. But I’m truly happiest out in nature, be it in the water, near a waterfall or a beautiful sunset, mountains or a forest. That’s where I feel the most alive and content.”

As for her greatest hope for the world:

“Peace,” she says unhesitatingly. “We must train our kids to become true citizens of the world. That means respecting other people’s differences instead of focusing on them to create hatred. To me, there’s no logic in wars. It’s oftentimes not about resources but about a religion or an ideological difference. I’m hopeful that one day all of us will wake up and realize that we are all connected as a human race and that we prosper far more from understanding each other and living harmoniously – rather than fighting. It’s common sense. Why wouldn’t we want peace? We have bad players in the world who create these wars and it’s counterproductive and self-annihilating. Everybody suffers from war.”

On an uplifting and positive note, Dee recalls the moments in her life that brought her immense happiness.

“The birth of my first son, Alex. It was such an impactful moment, as was the birth of all my children, but that first birth certainly stands out. Your whole world stops and changes when you give birth to your first child.”

Continuing with the memories of what brought her profound happiness, her eyes light up when she recalls this:

“The day that I married Tommy. I recall feeling so incredibly happy, and so filled with hope for the future. It took me 40 years to meet the man who was my soulmate. I was marrying my best friend, and it was the best feeling in the world. There’s truly no effort involved in our marriage because we are so compatible. We were both divorced with challenging first marriages, and we knew exactly what we didn’t want as we walked into our second marriage. We were so incredibly grateful to God that we got this second chance at happiness. Our relationship is steeped in love, respect, companionship and compatibility.”

Dee’s affirmation of the ingredients that bring us our greatest happiness is fitting for this time of year. May all of us welcome in 2025 with renewed hope, gratitude for what we have, and an abundance of shareable love.

Our gratitude goes out to Iconicfocusmodels NYC/LA

IG: @MrsHilfiger