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On a chilly afternoon in Sydney, a discreet parcel landed on my desk. Unassuming from the outside, it quickly revealed the unmistakable flash of red, white and blue I’d recognise anywhere as Tommy Hilfiger’s signature. But inside was something surprising: a beautifully crafted wooden box of dominoes—or as I would soon discover, an invitation to an exclusive island getaway…
When Tommy Hilfiger whisks you away for summer, you say yes and remain prepared for an adventure unlike any other. Over four days, Soho Beach House Canouan in St. Vincent and the Grenadines became the Tommy Hilfiger Resort, a slice of paradise nestled between turquoise waters, lush foliage and golden sun. Plucked from the grind of city living, I was dropped in the middle of this oasis with nothing but a brief of “pack light”. Filled with adventure, tranquility and the kind of views that make you rub your eyes, the Caribbean jaunt became a playground for guests of the brand to live and experience the new summer collection, putting looks to the ultimate test throughout an itinerary of sunny boat excursions, island soirees, intimate dinners and plenty of dancing.
From the very first moment, stepping barefoot onto warm wooden decking as the salt breeze rolled in, it was clear this wasn’t to be a passive presentation of a new collection. The island itself would become the runway. The Spring/Summer 2025 line didn’t hang static on rails or in a showroom, but was tested against boat winds and tropical heat, balmy evenings and impromptu dance floors, proving its worth in the very conditions it was designed for.
Each day began gently. First with a sunrise swim (jet lag is not a problem when it means having an entire beach to yourself), followed by coffee taken on a terrace overlooking the sparkling waters. Across the sand, hammocks swayed next to volleyball nets and rows upon rows of sun loungers. But the real theatre unfolded in the styling.
The guest list at The Hilfiger Resort naturally read like a who’s who of beautiful people. There was Patrick Schwarzenegger, fresh off his buzzy turn on The White Lotus, along with his fiancée, supermodel Abby Champion. Other actors, including Madelyn Cline, Lukas Gage, Michael Rainey Jr., and Anupam Tripathi, as well as influencers like Gabriella Brooks, Irene Kim and Noel Robinson. Watching everyone interpret the collection was like observing a living lookbook, played out in real time, against a backdrop of sand, sea, and rum cocktails. As they emerged one by one, ready for the day’s adventures, each was dressed in their own version of Hilfiger’s new uniform. An in-the-flesh lesson in vacation dressing: practical yet polished, the sort of pieces you could wear straight from snorkelling in Tobago Cays to cocktails on the jetty.
Tommy Hilfiger’s global CMO, Virginia Ritchie, put it well. “The Hilfiger lifestyle is about embodying a spirit of relentless optimism, embracing the perfectly imperfect, and celebrating come-as-you-are confidence,” she noted. “The Hilfiger Resort is the ideal setting for an eclectic summer getaway done the Tommy way: effortless, elegant, and always with our signature twist on classic style.”
From the bold stripes in classic Breton blues to the crinkled cotton regatta jackets that managed to feel both archival and of the moment, the maritime codes were clear, but so too was the lightness. Fabrics were chosen not only for aesthetics but also for breathability, resilience, and ease, while silhouettes serve as canvases for individual style stories. One morning encapsulated this perfectly. As I walked along the beach, espresso still in hand, I noticed three guests—all wearing the same striped shirt. And yet, not one looked remotely similar. One had tucked theirs into tailored linen shorts with a knotted rope belt; another wore it oversized, sleeves rolled, with bikini bottoms peeking out beneath; the third had layered theirs beneath a fisherman knit, a raffia cap pulled low, and a beach bag slung across the shoulder. It was proof that Hilfiger’s classics, while grounded in preppy codes, are endlessly open to interpretation—an invitation for personal style to take the lead.
The soundtrack was no less considered. Music shaped the rhythm of our days, from Rodney Small’s steel pans riffing through soca, calypso and jazz to Sabrina Francis’s velvet-voiced Afro-Caribbean soul that held us all spellbound one buzzy night. By the time Jeverson unleashed his blend of funk and pop on the closing evening, any pretence of restraint had melted away. Barefoot and sun-kissed, we danced into the early hours, the collection moving as freely as the music itself.
Hilfiger’s design philosophy—effortless, enduring, elegant with a twist—came alive most vividly in the small details. Capri pants in checks and solids felt refreshingly new when paired with oversized knits; varsity jackets cut from leather and linen had an almost poetic ease when thrown over sundresses; deck-inspired turn-ups on chinos whispered of yacht life but looked just as at home on the dance floor. Accessories played their part in the fun: a knotted bandana here, a chunky rope belt there, a raffia tote embroidered with the TH monogram adding a flash of irreverence.
And wear them we did—everywhere. On catamarans, gripping hats against the wind with one hand and a Corona with the other. On day trips to Mayreau Island, where seafood was devoured with fingers sticky from piña coladas. On verandas at golden hour, where linen suits looked crisp against Caribbean sunsets. Even swimming demanded style: nautical bikinis layered under loose-knitted polos, and silk shirts worn open.
By the final evening, the spirit of the collection had reached its crescendo. An intimate beachside dinner hosted by Tommy himself and his wife, Dee, doubled as a birthday celebration for the designer. Disco balls mingled with the starlight, the sand became our dancefloor, and the collection transformed yet again—this time into evening wear, each guest showcasing their personal vision of summer glamour. The grand finale? A surprise afterparty at a local club that looked over the whole island.
As dawn broke and we prepared to leave, my suitcase (now very full) comprised dresses, trousers, shirts and a host of accessories, all softened by sea air and reverie. Touched by their adventures, and ready for their next.
While I’ve grown up on the water, beach dressing has always eluded me. The Spring/Summer 2025 collection offered a smorgasbord of holiday-ready heroes—the sort of easy staples that are comfortable yet refined, versatile yet chic. Fabrics are weightless and soft to the touch, but aren’t quick to wrinkle and don’t demand excessive caution. After all, that is the genius of Tommy Hilfiger that has seen his designs transcend eras and trends. His empire may be built on preppy codes, but its legacy lies in how endlessly those codes can be reimagined. At The Hilfiger Resort, surrounded by friends, fashion, and the infinite horizon, it was impossible not to feel inspired.
Shop the Tommy Hilfiger spring/summer collection below
