Watches -- 12 hours ago
Words: Zak Maoui
An innate passion for sailing has shaped much of American designer Tommy Hilfiger’s design philosophy. Take a look at any of his seasonal collections and it’s all too clear that he’s somewhat inspired by sports uniforms and their design codes. Nautical stripes, oversized polo shirts fit for life at sea and windbreakers in the classic Hilfiger red, white and blue have sat comfortably in the fashion brand’s collections since its inception. This passion led, quite inevitably, to Hilfiger officially embracing competitive sailing in 2003. “The open water and the yachting lifestyle have always carried a sense of freedom and adventure,” Hilfiger has said. “Since the early ‘90s, our collections have captured the spirit of the sea, embracing maritime influences and blending relaxed sailing-inspired design with timeless prep. This collection is a tribute to that passion, a modern interpretation of our nautical heritage that remains true to the pioneering spirit of the brand.”
This year Hilfiger took his admiration for those who sail the high seas competitively to another level when he announced that his namesake brand would become the official lifestyle apparel partner of the U.S. SailGP Team. This has not only included dressing the team, which includes the likes of Taylor Canfield, Mac Agnese, Mike Buckley and Peter Kinney, but also creating innovative, high-performance eyewear through the Tommy Hilfiger Eyewear division.
SailGP, while perhaps not as largely recognised a sport as say the F1, is a pretty big deal and its momentum is growing. Gentleman’s Journal sat down with Canfield and Buckley ahead of this weekend’s big SailGP race in Portsmouth, UK, to discuss their day jobs, the pitfalls of competing and, of course, partnering with Tommy Hilfiger.
Gentleman's Journal: How did you get into sailing? What made you want to do what you do?
Mike Buckley: I got into racing during my high school years at Tabor Academy. Once I started I was hooked. I always loved competing in sports and racing sailboats was the perfect balance for me. I love the fact that our playing field is the ocean and you are constantly battling mother nature!
Taylor Canfield: I got involved in sailing at a very young age. I grew up in the U.S. Virgin Islands, and sailing there is a big part of life there. Sailing is deeply embedded in the local culture down there. My father (Bill Canfield) is also a sailor and was always a big advocate for the sport. Before I can remember, I was always on a boat. I started racing competitively at a young age, and my love of the sport grew year after year. I moved to the U.S. for college, where I raced at Boston College, and from there started in the professional match racing and world tour circuits.I was always around the sport, and knew it would be part of my life in some capacity, but sail because I genuinely love the sport. I love the intensity of match racing—it's like chess on water, I’m very analytical and competitive by nature.
The opportunity to represent the Virgin Islands is also something I’m very proud of. I want people to know that sailors can come out of any country, whether it’s big or small. I have tremendous pride in being from where I am, and I’m very grateful for my roots.
What do you enjoy the most about what you do?
Buckley: Competing.
Canfield: There’s nothing like being out on the water, powered by nature alone. No engines. Just you, your teammates, the boat, and the elements. In match racing especially, it’s all about outthinking your opponent. Every second counts, every move is a calculated risk—it’s like chess with physical consequences. And it’s not easy at times, but that’s the thrill of it.
It’s also about the feeling: the freedom of being powered only by nature, the trust you build with your crew, and the places this sport takes you. I grew up on the water in the Virgin Islands, and to be able to turn that into a career—while still feeling that same thrill I had as a kid—is something I never take for granted.
What are you looking forward to most about the Portsmouth SailGP race?
Buckley: Nothing beats the adrenaline of race day! We’ll be flying 100 km/hour, close to the shoreline and in front of a packed audience on the British south coast. It’s always inspiring to see the fans come together and how much we’re growing with each race globally.
Canfield: The energy of the crowd, the speeds we’ll reach, and the pressure of tactical racing. Sailing in such a historic location is always special, and having passionate fans close to the action creates an electric atmosphere on the water. The tight, challenging course means it will be fast, intense and competitive — exactly what SailGP is all about.
What's the hardest thing about your day job?
Buckley: As a sailor it’s the unpredictability. We’re constantly adapting to changing wind, weather and sea conditions. It demands not only physical endurance, but sharp focus and fast decision-making under pressure. And in a high-performance arena, every small mistake can make a big difference — the mental intensity is just as challenging as the physical.
Canfield: The hardest part is staying sharp — physically, mentally and emotionally. In this sport, the margin of error is tiny, and the water is unpredictable; we need to react quickly and one small lapse in focus can cost the race. We’re always learning, improving and pushing ourselves. And the challenges are also what make it so rewarding!
Why do you think Tommy Hilfiger aligns with sailing?
Buckley: We're so proud of our partnership and collaboration with Tommy Hilfiger which actively embodies inclusivity, creativity and innovation. Sailing has been in the brand’s DNA since the very beginning, so their designs perfectly capture the spirit and sense of adventure that the sport represents. They fuse fashion and sport in a way that only Tommy Hilfiger can do, while making sailing more dynamic and accessible. On a personal level, Tommy’s energy and passion are palpable — I get goosebumps when I think about how we’re shaking things up together!
Canfield: SailGP is redefining what sailing looks like—faster, bolder, and more connected to culture than ever before,” Canfield told us ahead of the race. “Partnering with Tommy Hilfiger helps us capture that energy. The brand knows how to spotlight a sport, not just through apparel but through storytelling, platforms and global visibility. It’s not just about performance—it’s about impact, and that’s where the alignment really takes off.”
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