Onboard a local passenger ferry you will usually find a mixture of tourists and tired commuters. However, on Sunday night, a former Staten Island ferry, moored in New York’s lower Manhattan, welcomed A-listers, sports stars and hip-hop heroes as Tommy Hilfiger took over the vessel to unveil his latest collection.

For a label devised in the Big Apple, the choice of venue that boasted views of the city’s skyline including notable NY landmarks such as the Brooklyn Bridge, could not have been more fitting. It also served as a signifier of Hilfiger’s power. Not many designers could get the K-pop band Stray Kids, Vogue’s Anna Wintour, Blackpink’s Jisoo, the track and field Olympian Gabby Thomas and three members of the Wu-Tang Clan to cross the gangway of a decommissioned and tired-looking ferry boat from the 1960s.

The original interior of the MV John F Kennedy, all teal-coloured walls and brown wooden benches, was left intact but life rings were emblazoned with Tommy Hilfiger. Deckhands dressed in smart white polo shirts handed out boxes of caramel popcorn and bottles of ice-cold Diet Coke as a 500-strong crowd took to the top deck.

Hilfiger described the collection as “the new American prep wardrobe”. The opening look featuring low-slung grey check trousers, a red check shirt and baggy white blazer, set the tone. This is a brand rooted in maritime. The red, white and blue logo that Hilfiger created in 1985 riffs on the semaphore flag system. His first show almost 40 years ago was nautical-themed. But Hilfiger avoided leaning into nostalgia.

In a preview, he outlined three key elements; “Shapes, fabrics and styling details”, which he used to give preppy staples a modern update. This meant chinos and sailing shorts came wide-legged, not tapered. Shirts featured vertical stripes in contrasting colours spliced together. Nautical jackets in generous proportions and oversized pointed lapels were worn with low-slung jeans. Hand-knitted jumpers and cardigans with marine rope-inspired TH crests were either supersized or cropped to above the navel. Rugby tops and varsity jackets were remixes of his 1990s hits championed by hip-hop artists.

Instead of deck shoes there were backless slippers teamed with socks and in place of boater hats came raffia baseball caps. Much of it was informed by Hilfiger’s own experiences at sea. He recently sold his 203ft superyacht Flag, which he first acquired in 2017 to spend summers coastal hopping from Portofino to Porto Cervo. Hilfiger described the style as effortless. “You could also call it easy luxury.”

While yachting is a hobby of the top one per cent, the aesthetic plays into a wider old-moneyed trend that consumers, including a gen Z cohort, desire. “Preppiness is definitely back,” Hilfiger said. “But it never really goes away. It’s casual and comfortable but it’s acceptable to be worn anywhere. It’s part of the heritage of American fashion.”

Hilfiger sold his company to PVH in 2010 for $3bn but the 73-year-old continues to lead the design team and creative vision. It’s a ship he wants to captain. “I want to build a global lifestyle brand,” he said. “We have yet to conquer home. There is more to be done in beauty. Our women’s business has the opportunity to become even bigger.” And while he’s currently shopping for his next superyacht, Hilfiger has no desire to set sail permanently. “I would be bored. And I think retirement is probably the beginning of the end.”

Hilfiger is now part of a triumvirate of American designers that are recognisable by their initials alone. But with Calvin Klein on a hiatus and Ralph Lauren choosing to host an off-calendar show to a smaller audience in the Hamptons, Sunday was an opportunity for Hilfiger to take the reins. A surprise finale performance by Staten Island’s Method Man, Ghostface Killah and Raekwon was a triumph. But Anna Wintour returning a fist-bump to Method Man was the final fashion coup d’état.