“I’m sick of fashion,” Tommy Hilfiger says jokingly. “I’ve been doing it for too long.” It’s a sunny day in late July and the 62-year-old designer is padding around his temporary home in Greenwich, CT, barefoot, waiting for his wife, Dee, to finish getting ready. “My real passion is flipping houses,” he adds with a smile. For the last several months, the couple has been busy renovating their Round Hill property, with the hope of being finished by the holidays.
Dressed in crisp white jeans and a cotton chambray button down, Tommy bounces from room to room offering pastries and coffee to his staff, catching up on work emails and playing with their 4-year-old son, Sebastian. He’s the picture perfect host in the picture perfect setting. A vintage Mercedes-Benz 280SL sits in the driveway alongside an Enzo Ferrari; a boat is docked in the Greenwich Harbor out back. “Go downstairs, enjoy the movie theater,” he urges. “We just made fresh popcorn.”
“It was love at second sight. We both have children from our prior marriages on the Autism spectrum so that was one of the things we bonded over.”
Moments later, Dee, 46, descends the staircase wearing a white long-sleeved dress and black knee-high boots, and his face lights up as if he’s seeing her for the first time. “Was it love at first sight?” I ask. “For me it was,” he replies with earnest sincerity. “She… had to sort of figure out who I was,” he continues before trailing off again. The two giggle and exchange a knowing look before launching into the tale of how they first met.
It was the summer of 2005 and both Dee and Tommy were vacationing in celebrity and socialite hotspot, Saint-Tropez. “I was on the beach with my two children and his yoga instructor started talking to me at the bar when I was trying to get change,” she explains. “Tommy was wearing sunglasses and standing with two other guys, so I didn’t realize who he was right away. When I found out it was Tommy Hilfiger, I assumed that I would be going on his boat with he and his boyfriend. I wasn’t even aware that he was a straight designer! So no, it was not love at first sight.”
The two became fast friends, bonding over shared interests and swapping stories about their children. Tommy has four from his previous marriage: Ally, 28, a downtown New York City girl-about-town; Rich, 23, a LA-based musician; Elizabeth, 20, a student at Rhode Island School of Design, and Kathleen, 18, a boarding school-student. Dee’s two teenage boys, Julian, 16, and Alex, 18, from her first marriage to Italian tennis professional, Gianni Ocleppo, both attend school in Italy. 
“It was love at second sight,” Dee clarifies. “We both have children from our prior marriages on the autism spectrum so that was one of the things we bonded over.” Ever since, the two have joined forces to raise awareness and funding for the disorder, even serving on the board of the national advocacy organization, Autism Speaks. “Tommy has done a public service announcement for autism and he’s also done a commercial and print ad. We reach out and annoy all of our wealthy friends to donate money too,” Dee reveals. “I donated a whole bunch of handbags to Autism Speaks and so 100 percent of the proceeds went towards autism.”
After only five years together, the pair has forged a powerful partnership, sharing passion projects, ideas and inspiration. “I consider Dee my muse,” Tommy divulges. “Every time we do a collection I think about what would look good on her, what she would wear and how she would wear it. I have to say, I have never met a woman who fits into everything so perfectly.” Despite Dee’s protests, Tommy continues to praise his svelte and stylish wife. “The week before the runway show we look at all the styles and everything she tries fits perfectly,” he exclaims. “We have to alter them for the models.”
And when the time calls for constructive criticism, Dee isn’t afraid to critique her husband’s designs. “I definitely make my opinions known,” she asserts. “I say, ‘I don’t like it. I hate it.’” He listens. “I know she has great taste,” he admits. “Plus, she’ll tell me the way it is. A lot of people will say, ‘Oh, it’s great’ and really not like it. But she’ll tell me exactly what she’s thinking.” It’s this sort of open, honest and collaborative communication that has made Dee and Tommy a true New York power couple. They finish each other’s sentences, compliment each other’s everyday style and support each other’s career endeavors.
For Dee, it’s two new accessory lines: one comprised of high-end handbags (currently available at Harrods), and another for HSN, featuring moderately priced coats, shoes and purses. “We use a lot of plaid, leather and faux furs. I think all the materials look high-end and luxurious,” she explains. “A lot of my inspiration comes from vintage. I’ve also taken ideas from my own wardrobe. I designed this line for the woman that really wants to look chic and look like a million dollars, but does not want to go broke trying to achieve that.”
“The smartest business decision I ever made was to find a niche in the market and stick to it over a long period of time. The second smartest was to bring in great partners.”
For Tommy, it’s continuing to grow his brand of classic, cool, American clothing. Though he sold the corporation in 2010 to Phillips-Van Heusen, he still retains complete creative control over all the designs, with an emphasis on the runway collections. “The smartest business decision I ever made was to find a niche in the market and stick to it over a long period of time,” he reveals. “The second smartest was to bring in great partners. They were very helpful in many different ways. It was like a band—you needed a guitarist, a drummer, a bass player and a singer—so I brought in a group of partners that all had specific strengths. We really worked together harmoniously for so many years.” 
Despite his unparalleled success in the fashion industry, Tommy recalls one design risk that completely backfired. “In the ‘90s I was chasing the modern minimalist trend so I tried to make the line more modern and sleek,” he remembers. “My customers completely pushed back. They really wanted to stay with preppy, colorful, cool designs. It was hard to rebound from that, but if I hadn’t tried it, I would always wonder. Luckily, I got it out of my system, made the mistake, and came back to who I really am.”
Even though Tommy may have a clear idea of who he really is, much to his delight, his fans often do not. “We were at Harlow restaurant recently and a guy came up to me and said, ‘I just got into town and I ran right to your store and bought a bunch of shirts and that’s all I wear. I love your shirts… I love the horse,’” Tommy recalls. “I smiled politely and said, ‘Oh, thank you very much.’”
“Ever since he let his hair go white, he’s been mistaken for Ralph [Lauren] quite a bit,” adds Dee with a laugh. Despite the reoccurring case of mistaken identity, Tommy says he has nothing but respect for his creative colleague. “We’re friendly and chat when we see each other,” he admits.
Though there’s never a shortage of fashion events and parties in Manhattan, the pair prefers to stay out of the limelight and enjoy romantic dates at Harry Cipriani before retiring to their penthouse apartment in the Plaza hotel. They’re also in the process of building a vacation home in Golden Beach, an oceanfront community in Miami. “We’re building an art gallery in our Miami house because we have so much great art in storage that we really don’t have room for today,” Tommy concedes. “I love art, it’s my passion.”
Between collecting art, designing fashion, flipping real estate and raising a toddler, the Hilfiger’s definitely have their hands full. But they couldn’t imagine it any other way. “Set a goal,” Tommy says, “and never give up.” ∎
