Style Savvy

Good things are worth the wait. That’s the approach Dee Ocleppo Hilfiger took to the luxurious but painstaking remodel of her family’s Palm Beach home, Coral House. “We were in two temporary homes. It took us three years in the middle of COVID-19 to actually get here,” says Ocleppo Hilfiger. “It was a long, arduous process, but now that we’re here, this is home base.”

Her favorite part of living in Palm Beach, she says, is the sense of community. “It’s very safe and quiet and not as hustle and bustle as Miami and Fort Lauderdale. I know all of my neighbors.”

Coral House’s artful, exotic design reflects its name. “We did the house in coral stone,” she explains. “We love coral stone because we also have a home in Mustique [a private island in the Southern Caribbean] that’s on the water with a lot of coral stone and we love how it ages over time. It has a certain patina that’s really beautiful. We did coral stone stairs, and we added a lot of pecky cypress ceilings. We wanted it to feel classic Palm Beach but with natural materials and colors.”

We, of course, refers to Ocleppo Hilfiger’s husband, Tommy Hilfiger, and their blended family of seven children. Although married to one of fashion’s most influential American designers, Ocleppo Hilfiger has established herself as an innovator in her own right. Her synonymous line of handbags, shoes and accessories offer styles inspired by Italian craftsmanship at attainable price points. She also serves as creative director of Judith Leiber, the iconic label famous for its playful couture purses. The key to double duty as the head of both brands: Zoom. “Zoom lets me be efficient with my time. If you’re organized and can be efficient, you’d be amazed at how much you can get done.”

Prior to anchoring in South Florida, the couple spent a whirlwind few years moving from place to place. “We had been based in Greenwich, Conn.,”

she explains. “And at one point we had an apartment in The Plaza Hotel [in New York City] which we sold because we just never slept there; we’d always drive back to Greenwich. When we lived in Greenwich, we also had a home in Golden Beach, in North Miami [Beach] which was like a secondary vacation home. During COVID-19 we sold both and were actually for a while living out of hotels. After about a month, I was like, ‘We can’t do this,’ so we wound up in one of the temporary homes while the work to Coral House was being done.”

Born in Cleveland, Ohio, and raised in East Greenwich, R.I., Ocleppo Hilfiger spent a pre-digital childhood engrossed in glossy magazines. “My mom would buy magazines and we would get catalogs and, from a really young age, I was fascinated by all that. I remember being fascinated by Vogue and National Geographic in particular.”

Shortly after graduating high school, fashion came calling when a professional photographer spotted Ocleppo Hilfiger in her class photo in the local paper. “He happened to be in town working on the Bonne Bell campaign and he saw this picture in the paper of me and called the school to find out who I was. It was a fluke thing. I had never thought about modeling, I never thought I could do that.”

One of her first jobs was modeling in the  Rhode Island School of Design (RISD) runway show, where she paid close attention to the design process. “The students had all these creative ideas. I thought it would be cool if I could do that one day but didn’t necessarily think I could because I didn’t go to fashion school.”

It wasn’t until years later, at her husband’s urging, that Ocleppo Hilfiger took a chance on herself. “Tommy said to me, ‘You know, I didn’t go to fashion school. You have great taste and a great eye and you know this business.’”

A favorite personal accessory served as the blueprint for her debut item. “I used to carry this Pappagallo bag that you could take the covers off. It had buttons which you could undo to change the cover and reverse them. Tommy thought it could be a whole business. So, I made some prototypes and that’s how I got started. Mindy Grossman was the head of HSN at the time and I walked into her office and showed her the bags. She loved them and she was the one who gave me my big opportunity. My first break into the fashion industry was on HSN.”

Before long, Ocleppo Hilfiger expanded her line of bags and added shoes. “I had so much encouragement. Not only from my husband but from others in the industry. When the people around you are kind and encouraging, you don’t want to stop.”

Her own line and Judith Leiber have distinct aesthetics, the former being a mix of quiet, affordable luxury and the latter glitzy, pricey and tongue-in-cheek. “Each represents a piece of me,” she notes, “they’re both coming from my mind. There are different teams and different brands, but it always comes from my idea of what looks good.”

She often draws on travel for inspiration. “The more you can get outside your frame of reference and see the world in a larger way, the better it is for you creatively. Seeing different cultures can trigger something in your mind to try something different.” Among her favorite destinations: Turkey, Morocco and, of course, Italy.

While her lifestyle is undeniably aspirational, Ocleppo Hilfiger shares relatable, service-driven tips on her blog, “Deescover,” including holiday gift ideas, healthy recipes, product recommendations and rule-of-thumb fashion, decor and design suggestions. “I try to offer practical advice. We all have homes and we all have to cook, so hopefully my advice is helpful.”

The couple also offers significant time and generosity to a number of causes, including Next for Autism, a condition that affects three of the Hilfigers’ seven children, the Breast Cancer Research Foundation (BCRF) and amfAR. “We lend ourselves to a lot and that keeps us busy,” she says. “We put a lot of effort into our philanthropies.”

Take away the red carpets and the high-profile, jet-setting lifestyle, Ocleppo Hilfiger says that by far, her most valued assets are health and family. “The quality of your life has a lot to do with the quality of your relationships,” she notes. “I’m very happily married and I feel really blessed and grateful to have found someone whose values and moral compass I admire. So, I’m very grateful that I get to share my life with an exceptional human being and that gratitude carries through everything. There are also my friends, my relationship with my family. Take away everything, I’m most grateful for that.”

As a designer, a home line seems like the next natural evolution of her brand. “Tommy and I have bought, sold and decorated many, many homes. It’s a huge creative outlet for us. It’s authentic to me and my lifestyle and what I do. We’ve done a pretty good job at it, so, yes, I’d love to do it.”

Her No. 1 piece of advice for anyone, whether they’re considering a subtle refresh or complete overhaul? “Slowly layer,” she emphasizes. “Sometimes people try to do too many things, too many styles in one room. It’s almost like getting dressed with jewelry. Start with one thing. If you want to paint your walls a beautiful color, start there and then slowly layer. You can always add more.”