As celebrated US fashion designer Tommy Hilfiger trades in his 62-metre superyacht Flag, BOAT reflects on a 2023 interview with the fashion mogul. For him, his yacht was a source of inspiration, a place for relaxation and a trigger for innovation – the epitome of his enduring ethos, he tells Lucy Dunn.
The Mediterranean in summer is a veritable home away from home for fashion designer Tommy Hilfiger and wife Dee – or should we say yacht away from yacht? “We bump into friends from America literally every day,” Hilfiger tells me. “Right now we’re anchored next to neighbours of ours from Palm Beach and we’ve just had lunch with friends from Manhattan. It’s great, we’re not complaining!”
His 62-metre Feadship Flag is moored in Monaco and Hilfiger is speaking to me via video link from his office on board. Baseball cap on and sleeves rolled up, he’s in holiday mode – up to a point. Between catwalk shows and new collections, summer is traditionally downtime for designers and he is using this time to coast hop – “Portofino! Capri! Porto Cervo!” he says, reeling off his favourite places – although his diary is never completely clear. “Much to Dee’s dismay,” he laughs. “And the kids are like ‘Dad, are you on the phone again?’ But I love working, I love my brand. I’m very involved.”
Hilfiger’s story is the stuff of American dreams: a suburban kid from Elmira, New York, who opened a small clothing store in 1969 selling bell-bottom jeans, and who went on to create a multi-billion-dollar fashion empire. The idea for his label came to him in a dream in 1972, he tells me. “I could actually picture in my mind what I wanted it to be and what I wanted the clothes to be. It took a while to get there because there were ups and downs financially, but I’m realising that dream today.”
His vision – to give all-American preppy clothes a cooler edge and team them with more streetwise sportswear – has never wavered. In the pop-culture-obsessed era of the early 1990s, his clothes appeared across the fashion, music and entertainment worlds, and this strong connection to culture still runs through the brand today.
The brand is spearheaded by a distinctive red, white and blue logo. I ask Hilfiger about its nautical meaning, whether the white and red are taken from the International Code of Signals flag for “H” (for Hilfiger, and which when hoisted means “I have a pilot on board.”) “You noticed!” he says, delightedly. “Yes, when I started, I wanted something nautical because the aspirational lifestyle is so linked to yachting. I wanted something that meant something; something I would always be identified with.” In his 2016 memoir he reflected on this further: “I’ve always loved the look and feel of yachting and sailing and being on the sea,” he wrote. “It conjures places in the world infused with wealth, warmth, romance, excitement, inspiration and aspiration: Newport, Nantucket, Portofino, Saint-Tropez. Just as in my dreams as a boy, being on the water is all about escapism... The good life is something everyone wants.”
He was chartering a yacht in 2005 when he met his second wife Dee Ocleppo on a beach in Saint-Tropez. They married three years later. The couple both have children on the autism spectrum (Hilfiger was one of the first mainstream designers to launch an inclusive adaptive clothing line for adults and kids with autism and special needs) and this was one of the things they initially bonded over, along with a shared love of fashion and design. (Dee later went on to launch her own affordable luxury accessories line and transformed the Judith Leiber label into a high-octane handbag brand beloved by Rihanna, Jennifer Lopez and Beyoncé.)
With the nautical-inspired logo in place, when Hilfiger bought his own yacht in 2017, he already had the perfect name: Flag. He got her from friend and business partner Lawrence Stroll. “I’d been a guest of Faith (Flag’s former name) many times and loved it and thought that if he ever decided to sell, I’d be the guy to buy her.”
With the help of Ralph Lauren creative director Chahan Minassian, Stroll had completely refitted Faith from top to bottom. Hilfiger loved what he’d done: “Firstly, Feadship is by far my favourite yacht builder in the world. But the way it was refitted was fabulous: classic, but with modern conveniences and a modern look. It was right on target in terms of the right amount of, I would call, decorative ambience with the right amount of casual space, but at the same time a beautiful old-world classic.”
Hilfiger had already done his homework by chartering a selection of yachts, including the iconic Christina O as well as Diamond A, Huntress and Galaxy. He spent time working out what he did and didn’t like. “As a designer, I’m very particular about things like furniture, carpeting, bathroom fixtures and colour scheme, and I don’t want any of my environments to be obnoxious or overdone,” he explains. “But I also don’t want them to be too minimalistic; somewhere in the middle. And of course I wanted it to be liveable for my family as well as chic and beautiful for my guests.” (Ever the businessman, Hilfiger planned to charter Flag when not using it himself.)
Stroll made Hilfiger wait six years. “Then one day he called me and told me he was building another boat and asked if I would be interested in buying her. I said ‘One hundred per cent!’ So within a four-week period we built a deal and I took over Flag when he took delivery of the new Faith.”
Hilfiger and Dee then set to work, enlisting Minassian again, this time to make Flag’s interiors their own. “We did a lot of work on the galley (Tommy and Dee are both big food lovers), redesigned the bedding, soft furnishings. I also made the tenders, slide and jet skis Tommy Hilfiger colours. I wanted everything to look cohesive.”
The result is elegant yet modern, luxurious yet not ostentatious or showy. Rich mahogany trims and furniture are contrasted by crisp white leather, gleaming fixtures, and finishes in chrome and marble. Hermès sheepskin chairs, cosy sofas and deep cream carpeting underfoot add a palatial hush. Graphic-print accessories lend a nautical vibe, while sleek modern art adds subtle impact: the highlight, a light sculpture called Portal by artist Chul-Hyun Ahn hanging in the formal dining room, cleverly mirrors the plasma TVs hung around the yacht. The final touch in Flag’s Hilfiger-ification was the logo, which sits aloft next to the yacht’s name on the superstructure. There’s no doubt this is Hilfiger’s boat.
Chartering a yacht can sometimes feel like either intruding in someone else’s space or stepping into a commercial blank canvas that has no personality, but Flag is neither, deftly balancing intimacy and style throughout its four decks and seven guest cabins. It is advertised to sleep 12 guests for charter, but will comfortably sleep 18, and there is a 17-person crew.
Hilfiger knows how to build a successful charter business. “Make sure you have a great crew like mine who pay attention to detail, who are watching every guest and thinking ahead, second-guessing their needs,” he advises. “Also, it’s so important to have great captains who will lead the way, who inspire the crew and motivate them. If you have these then you will have guests coming back every year like we do.”
And if you were trying to persuade someone who was thinking of chartering but dithering? “I would tell them ‘Just do it,’” Dee says. “You’ll never experience service and privacy quite like when you charter or own a yacht.” You’ll also never have a holiday quite like it, she adds. “Once, when we were in the Bahamas on vacation with our son, Sebastian, we were parked in front of a beautiful tiny island with crystal-clear water. I was learning how to e-foil when a small pod of curious dolphins came up right behind me and swam around me.”
The family’s favourite room is the lounge on the bridge deck aft, which has the best views of the sea. “We call it the blue salon,” says Hilfiger. “It’s like a movie theatre with a big-screen TV with a bar. We often end up there in the evening. I also like the dining table on the aft deck because that’s where we have the most fun having dinners with friends and family. There’s a lot of chatter and a lot of, I would say, inspiration.”
Hilfiger thrives on inspiration, and even after decades at the helm as principal designer he is still very much the eyes and ears of the brand, continually driving it forward by embracing the new. He was one of the first designers to tap in to the power of celebrity endorsement, via famous fans like Snoop Dogg and P Diddy, and he makes a point of continuing to collaborate with those at the heart of the zeitgeist, from small streetwear brands to Formula One. “You have to look at everything – everything,” he stresses. “I call it F.A.M.E: fashion, art, music, entertainment, plus influencers, sport. It’s what’s making the clock tick now.”
Of course, in this TikTok age fashion is about more than clothes, and at 72 Hilfiger joins a select group of impressively tireless greats including Vera Wang (74), Giorgio Armani (89) and Ralph Lauren (83) who continue to expand their empires in new ways (Armani even collaborated with The Italian Sea Group to design a 72-metre yacht last year).
When it comes to yacht-linked brand extensions, however, Hilfiger arguably got there first with Flag. Lewis Hamilton, Bella Hadid and Kendall Jenner are often seen gracing her decks, while Kardashian “momager” Kris Jenner and boyfriend Corey Gamble are also regular guests.
I ask what’s next for the Hilfiger brand. “Well, fashion is something I love and have been doing for 40 years,” the designer replies. “But in the last 20 years, I’ve been really engaged in decorating and developing my residences, so it’s very important to me that I mix the two together. I would like to continue to develop Hilfiger into a total lifestyle brand.”
So branded residences, cars, hotels, maybe even a line of boats? He nods. “I find it visually exciting to look at a space and say, ‘OK, what can we do with it?’ There are so many possibilities if you have a vision and a creative idea.”
One major decision in recent months is that Tommy and Dee have decided to put Flag up for sale. The couple have seven grown-up children from their previous marriages (Sebastian, 14, is the son they share), and when you add partners and a grandchild into the equation family get-togethers can become quite busy. “When you have so many guests, you need a little more space,” he says. “If I get the right price, I’ll sell it and maybe build something larger. But if I don’t, I’ll keep it and be very happy because it’s an amazing boat.”
If he sounds tinged with seller’s remorse, it’s only because he loves the yacht, calling it his “most prized possession”. “One of my friends who has a Feadship called me last week. He said ‘Why would you even think of selling? You have one of the best Feadships ever built!’ I said, ‘You know, I was thinking maybe a little bit wider, a little bit bigger.’ He said, ‘Don’t be stupid, you’ll never be able to replace it.’ But we’ll see...” He shrugs, laughing. “Everything is for sale, sort of – homes, cars, properties – but we’re very happy and we’re doing well!”
If he sells Flag, what will he do with his downtime then? Is there anything aside else that could drag him away from his laptop?
“Silverback gorillas in Rwanda,” Hilfiger says without hesitation. “I’m obsessed with animals and nature. I’d like to go on some deeper safaris, go off-grid.”
So he’s not hanging up his baseball cap quite yet?
“Noooo! I’m still young! I’ve still got so much to do!”
And I think I’m inclined to believe him.
Flag is available for sale and charter with Burgess and will be available to view by appointment at this year’s Monaco Yacht Show.
First published in the October 2023 issue of BOAT International. Get this magazine sent straight to your door, or subscribe and never miss an issue.
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