Unapologetically Dee: A Force All Her Own

From model to creative force, Dee Ocleppo Hilfiger opens up about her new Lilly Pulitzer collaboration, her layered path through love and business, and the power of becoming yourself — on your own timeline.

BY LAURA VALLINA

      PHOTOGRAPHY DIEGO MENDOZA 

      STYLING CHARLIE RINCON

HAIR AND MAKEUP JULIANA GONZALEZ

SET DESIGN MARTINA HOYOS

     PHOTO ASSISTANT HERMES ABREU

                                                      SHOT ON LOCATION IN PALM BEACH, FL

 Photo Credit: Diego Mendoza

In her Palm Beach estate, where coral walls shimmer under Florida light and vintage art meets modern design, Dee Ocleppo Hilfiger moves through her world with effortless confidence. It’s here, surrounded by color and character, that her latest project with resort wear icon Lilly Pulitzer was born: a limited-edition capsule collection that feels as vibrant as Dee herself. But this is just one chapter in a much larger story.

Hilfiger is the creative director of legendary accessories brand Judith Leiber, as well as the founder of Mrs. H Designer and DO by Dee Ocleppo.

Yet what makes Hilfiger a true icon isn’t just her career, family or brand. It’s her unapologetic authenticity, whimsical aura, and rare ability to mix class with raw honesty. She’ll tell you exactly how she feels — no performance, no filter — just the confidence of a woman who knows who she is. Like every grand woman, Dee is layered and complex. When Haute Living sat down with Mrs. Hilfiger at her Palm Beach estate, Coral House — a striking, coral stone, ivory Spanish-Mediterranean-style home — her layers unfolded.

“I’ve had about 90 lives,” Hilfiger says with a laugh. “I call my 20s my dumb years — I did the dumbest things. So many mistakes. I’m just glad I made it through them alive.”

She speaks about that time with both humor and hard-earned perspective.

“I was anxious in my 20s, probably because of some of the choices I made. Maybe it’s just the frontal lobe developing, but confidence definitely comes with age.”

Her candor is disarming; refreshingly honest. From her modeling days in Paris to marrying her first husband and having her first child in her mid-20s, navigating a divorce in her thirties, meeting her current husband, fashion designer Tommy Hilfiger, in her late thirties, and launching her eponymous brand in her forties, Hilfiger’s journey proves that life unfolds on its own timeline.

Photo Credit: Diego Mendoza

By her fifties, Dee had become co-owner and creative director of Judith Leiber and launched Mrs. H, her home décor and lifestyle line for QVC.

Every chapter of her career has built upon the last — a reminder that success isn’t about timing, but about trust, growth, and staying open to what’s next.

“When I divorced my first husband, that was extremely difficult,” Hilfiger confesses. “After having to rebuild my life, living alone, and dealing with sharing the raising of kids, I had to trust the universe that there was something better and that I would come out the other end happier.”

When asked how she quieted her anxiety, she pauses.

“Time, sadly,” she says.

The simplicity lands harder than any prescription could. She could have said Pilates or meditation; instead, she offers honesty — unvarnished and real.

Sitting in her coral bar, where warm, terracotta-tinged walls are framed with gilded trim, and overhead a dramatic palm-inspired chandelier dripped with crystal fronds that caught and scattered the light across the room, I realized the symbol she represents: real success. I was surrounded by it — it was right in front of me. But it doesn’t happen in a swipe or a scroll. Your TikTok “For You Page” may sell you the overnight success fantasy. The real thing? It takes overcoming hurdles — built slowly, deliberately, and over time. Dee Hilfiger embodies what a true woman is: someone unapologetically herself, unafraid to acknowledge imperfections, and confident enough to speak the truth about life’s messy, beautiful reality.

“I was very anti-marriage after my first one,” Mrs. Hilfiger stated. “I thought, yeah, not doing that again, not ever going through that again. It’s very hard to open yourself up again, trust love and being loved again, and what that might entail. And it’s scary, especially after you’ve been through a divorce with children. Thank God it’s worked out beautifully,” she added.

Dee met Tommy in her late thirties in Saint-Tropez over Bastille weekend — an encounter that would change everything.

“I was living in Monaco at the time, and I drove to Saint-Tropez with my kids to spend the weekend,” Hilfiger recounts. “I was at the beach, and his yoga instructor came up to me, introduced me to all these guys. They were wearing sunglasses. And the instructor said, ‘This is Alex, this is Henry, and this is Tommy.’ He didn’t say, ‘This is Tommy Hilfiger.’”

Later that day, Dee got a call.

“Tommy said, ‘Hi, you just met me, this is Tommy Hilfiger,’” she recalls. “I understand you said you couldn’t come to the party because you don’t have a nanny, but if you bring your kids, I’ll have the crew make them chicken fingers.”

[For the record, Dee hadn’t given him her number; he’d gone through his yoga instructor to get it — determination clearly paid off.]

Given Dee and Tommy’s shared passion for real estate and interior design — evident in their book Hilfiger Homes, with a foreword by Anna Wintour, which showcases seven of their uniquely designed estates — I assumed their shared creative DNA was what initially brought them together. But if there’s one thing I learned about Dee Hilfiger, it’s that she will always give you the realest answer.

“I just assumed he was gay, being a designer,” she chuckled. “Then that night of the party, I saw he was with another woman and they started kissing, so I was like, oh, that’s interesting. The next day, he invited me to lunch, and we started talking and realized that we both had children on the autistic spectrum,” Hilfiger shared. “That was the first thing we sort of bonded over. But I was trying to keep it in the friend zone, scared to open that door.”

But Tommy was persistent. Though they were continents apart, they kept circling back to one another. “I had him in a friend zone, and then he got back together with his ex-girlfriend,” she revealed. “You know, it was very difficult. I don’t know if Tommy made me feel the safest in the beginning; it had to be built over time. I wish it were that easy.”

Photo Credit: Diego Mendoza

Another refreshing truth. Love takes time, patience, and commitment on both sides to grow into something lasting. And Hilfiger’s message is a reminder worth holding onto. That’s okay. There’s no need to script a flawless story. The strength lies in the work, the honesty, and the willingness to build something real together.

We split up for a little while before we were supposed to get married,” Hilfiger confides. “But we kept coming back to it and working on it, and now we’re married and have Sebastian together. I think we both feel very safe now.”

Then, the coral door creaks open, and Tommy Hilfiger strides in.

“You didn’t ask me one question,” he jokes, before saying more seriously, “She’s my angel,” Mr. Hilfiger says warmly. “She’s having her moment. I’m so proud. Last night, I was watching her on QVC, and she spoke so well, and then seeing her doing all of this, I love it.”

And with that, he heads off to check on their son.

When it comes to family, Dee’s parenting is rooted in her grounded strength. “It’s important to always be there for your child growing up, but also still putting your love and creativity in other places in your life,” Mrs. Hilfiger says. “You know, he’ll walk by and see that mommy is working, but the same way he also knows that mommy is always there for him, I like him seeing me work because he needs to understand none of this is given, and for him to also see that I enjoy work.”

It’s the kind of balance so many women strive for, showing your child love and presence, while reminding them that ambition and joy can coexist.

Photo Credit: Diego Mendoza

She’s always designed with women in mind — her jeweled, playful-yetsophisticated Judith Leiber bags that not only start but sustain conversations. She brought us back to when they first bought the heritage brand.

“When we bought the brand, I would talk to people, and they all said the same thing. They were like, ‘My grandmother collected that,’” Hilfiger reflects. “I said to Tommy, we need to reintroduce the brand to a younger audience. I was looking at our archives and noticed they had a really fun cupcake bag and said, I really like this direction.

From a crystal-encrusted clutch shaped like a flying saucer to the Kardashian-Jenners’ lineup of personality minaudières, Hilfiger has helped guide the brand into pop-culture stardom. These dazzling creations — the kind that light up red carpets — may sparkle in the spotlight, but for Hilfiger, the real brilliance comes from the people around her. “Tommy was the one who supported and encouraged me,” she notes.

That support has allowed her creativity to flourish, including her latest project with Lilly Pulitzer, a collaboration that feels like an ode to Palm Beach itself. Think conch-shell pink, salt-pond blue, lounging alligators, martinis, and flamingos. Plus, a limited-edition Judith Leiber x Lilly bag (you heard it here first).

“The collection is actually a love letter to those two women, both of whom started American heritage brands — which there are not many of — who were very brave,” Mrs. Hilfiger points out. “In the case of Judith Leiber, it’s been around for more than 50 years. That’s a huge achievement in the fashion business.”

Photo Credit: Diego Mendoza

Dee Hilfiger is a businesswoman, model, mother, and global creative force — the creative director of a 65-year-old heritage brand who also happens to be married to an American fashion icon. How does one stay humble? For Hilfiger, wit hangs on the bathroom wall: an Alison Jackson photograph of Queen Elizabeth on the toilet — a cheeky reminder that, at the end of the day, we’re all the same. But humor isn’t the only British sensibility she embodies. Her life motto remains the timeless mantra: Keep calm and carry on. People often say that behind every strong man there’s a stronger woman. While true, Hilfiger is a force all her own. Her journey proves there is no single timeline for success; some take off in their 20s, others in their 40s or 50s. Her advice? Trust the universe. And with every new chapter, Hilfiger reminds us that class, substance, and strength are ageless.