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Island Life by Kristina Stewart Ward | 4th March, 2016 | Personalities

Palm trees hold pride of place in the British Colonial oasis Mr. and Mrs. Hilfiger inhabit on Mustique, an island renowned  for barefoot royals, artists and celebrities. Equally renowned is the casual chic of the lady of the house, a working mom who successfully juggles multiple homes in as many time zones.

The modern social nomad finds an ideal advocate in Dee Ocleppo, the busy mother of three, stepmother of four and wife of acclaimed designer Tommy Hilfiger who, herself, now designs a chic collection of handbags with classic silhouettes and interchangeable covers. It’s versatile, transitional luxury fueled by inspiration from Dee’s own breakneck pace while traveling for business and jetting between homes in Miami, Greenwich, and her beloved Mustique.

“We don’t entertain formally, this is where our patchwork family feels at home.” Dee Ocleppo

It is here in the British Colonial-style, family-friendly sanctuary nestled among Mustique’s largest palm grove, that three sprawling generations of Hilfigers gather several times a year to recharge – and it is here that Dee initially conceived of handbags geared to transition as seamlessly as she does. “The collection has it roots in the realities of travel,” explains Dee, detailing the fashion dilemmas faced by other women similarly pulled between different lives. Of course it’s a very nice problem to have, and no one seems more grateful for the world she inhabits than the Rhode Island native whose modeling career gave way to motherhood and now the role of accessories designer. “We can all relate to wanting our wardrobes to extend the way that we do ourselves,” she continues, detailing her early attempts at packing enough variety as she navigated between settings. Dee’s tightly edited collection now tackles these transitions with beautifully classic “lady” silhouettes that can be augmented with playful fringe, exotic skins and Technicolor fur – interchangeable covers that take on new personas while still offering economy of space for packing. Day-into-evening: check. Countryside-into-city-chic: done. Miami-bold-to-Mustique-boho: covered. The Spring Collection’s current wardrobe changes include python, croc, suede, raffia, fox fur, lizard and lynx, and no less than Beyonce, Kerry Washington and the Kardashians have been photographed carrying the infinitely customizable bags.

“Home is a sanctuary – a place you go to be surrounded by things that make you feel good.” Dee Ocleppo

So when Dee settles into island life in Mustique, what style does she herself opt for? “Oh, I suppose ‘glampy’ is the best word to describe my style out here,” she says laughing. “There are no paparazzi here, no gambling, no cruise ships coming through, not even stop lights on the streets – just shoes-optional dressing from morning until night. Out here we’re comfortable, practical, bohemian. Out here, everything slows down. Except the kids; this is a family home, with lots of kids running around.” Dee describes living at the home that looks every inch the hybrid of a Caribbean plantation and a British Colonial villa, a two-story coral stone product of four years rendering the designs of Mustique’s most famed architect, Oliver Messel. Dee’s husband Tommy commissioned Arne Hasselqvist to execute the plans on a pristine 10-acre, ocean-front estate that Tommy named “Palm Beach” for the 250 palm trees surrounding the house and lining the stretch of sand lying between the aqua blue of the pool and the Caribbean Sea. Local coral stone and mahogany wood were used for the structure highlighted by Palladian windows with painted wooden shutters. Hilfiger commissioned Colefax and Fowler to decorate the six-bedroom home in British Colonial but left room for the casual way the property would be used. “We don’t entertain formally,” says Dee. “It’s simple, primitive pleasures here: bicycles and golf carts to get around, swimming and long walks, fresh fish and barbecues, movies at night.”

“I come here to recharge, to reconnect with myself and family without city distractions.” Dee Ocleppo

While these activities might appear out of step for such a high-profile family, it seems that the Hilfigers weren’t the first international jet-setters to come here seeking peaceful island living out of the spotlight. The Duke and Duchess of Cambridge are among the current crop of royals to mix with Mustique’s compelling roster of bold-faced names, but it was Prince William’s great-aunt, Princess Margaret and her pal Lord Glenconner who blazed the original trail, the latter having found the idyllic island and colonized it for his enviable list of friends. He gave a 10-acre parcel of land to Princess Margaret as a wedding present when she married Lord Snowden, and commissioned Snowden’s uncle, Oliver Messel, to design most of the island’s first buildings. Tommy Hilfiger’s sense of provenance and context bares out in his use of Messel’s plans for his own home and his family all ascribe to the island’s low-key, barefoot charm.

On a typical trip, that means 7-year-old Sebastian sets the pace for the couple of ten years who agreed to install a pizza oven, soft-serve ice cream machine and a tepee perched on the beach—all of which are now coveted by the older siblings and adults alike. Dee and Tommy’s combined, sprawling family of seven children helps explain why their home in Mus-tique isn’t intended to be a shrine to perfectly manicured style. “We actually live here,” says Dee of their multi-generational brood, the family surely inspiring the Tommy Hilfiger brand’s endearingly chaotic, ongoing ad campaign: “Meet the Hilfigers.” And it turns out that calibrated chaos is precisely what Mustique’s laid-back lifestyle is ideally
suited toward.

“The colors and feel of the island, the travel logistics required to arrive – it all emerges in the designs of my collection.” Dee Ocleppo

Among the couple’s children are Tommy’s daughter Kathleen and Dee’s son Alex, both of whom are on the autism spectrum. Indeed, long discussions about their shared experiences with their children served as the kindling that eventually sparked their relationship ten years ago. The devoted parents have since done much to champion their shared cause publically, speaking up about the condition as well as the need to participate in the larger community supporting children and adults with autism. Tommy and Dee are both on the board of Autism Speaks (, the largest advocacy and research fundraising organization for the condition, and April is National Autism Awareness Month. Dee’s roles as an autism advocate and devoted mother are reminders of the multiple hats this sophisticated juggler wears as she navigates a life that takes her from fundraising, to design meetings, to parent-teacher conferences, to gala parties, and eventually – thankfully – to the calm of her Mustique sanctuary where she unwinds and possibly even dreams up her next big collection under the shade of a lazy palm tree.

It’s a world away from the city life that will soon beckon Dee and Tommy back to working on their respective, namesake collections, and because Dee’s designs are focused on making transitions and travel easier, looking the part is far from the hardest part about returning.

IssueGG Magazine 02/16
City/CountryMustique / Saint Vincent and the Grenadines
PhotographyBasset Images / Kate Martin