Welcome Aboard Tommy Hilfiger's Nautica-Nostalgia SS25 Show

Tommy Hilfiger's Spring/Summer 2025 show transported the audience straight into a world where 'preppy' reigned supreme and it did so in the most nostalgic way possible. Tommy Hilfiger brought back the essence of '90s America, an era when hip hop was surging through the streets, yet perfectly juxtaposed with the polished, preppy aesthetic of the yuppie crowd.

The show was a masterclass in creating a vivid sense of '90s nostalgia, with each piece evoking memories of the decade's fashion heyday. From the runway to the collection, the entire experience felt like stepping into the pages of a vintage Tommy Hilfiger Nautica-inspired catalog, complete with the carefree yet structured style that defined the era. It was a playful homage to the past, reminding us just how timeless the preppy look can be.

Keep scrolling for our full review.

WHERE: The SS25 show was set on the renowned and decommissioned MC John F. Kennedy at Pier 17 -- a legendary move, as this is the last remaining Kennedy-class ferry known for commuting passengers from Staten Island to New York.

WHO: Felix and Lee Know of the K-pop sensation Stray Kids made a striking debut at New York Fashion Week, joined by none other than Blackpink's Jisoo, adding a touch of star power to the event. The front row was just as dazzling, featuring the entertaining content creator Jake Shane, supermodel Winnie Harlow and America's beloved, Brooke Shields who beamed with pride as she watched her 18-year-old daughter, Grier Hammond, take her first steps down the runway.

But who truly captivated the runway? None other than Leon Dame, famed for his electrifying and unforgettable opening for Maison Margiela's Fall/Winter 2024 show. Alongside him was the stunning Mona Tougaard, adding her own grace and presence to the star-studded affair.

SEE: Tommy Hilfiger fully embraced the essence of '90s preppy America with his latest collection, leaving no stone unturned in capturing the scene. Imagine an Ivy-League kid spending the weekend sailing -- this is exactly the energy the pieces gave. The collection showcased everything from classic "Breton" and "Ithaca" shirting stripes to archival regatta jackets and utility pants.

The lineup featured staples like varsity jackets, tailored chino pants, double-pleated yacht shorts and hand-knitted polos, each radiating a timeless yet fresh feel. The looks were perfectly accessorized with playful neck-tie bandanas, laid-back baseball caps and hand-woven coastal slippers.

HEAR: The show came to a powerful close with Staten Island's own Wu-Tang Clan, perfectly in tune with the event's nostalgic theme. Members Ghostface Killah, Method Man and Raekwon delivered a high-energy performance that electrified the crowd. Adding to the atmosphere, Questlove returned to expertly curate the soundtrack, filling the venue with timeless tracks like "C.R.E.A.M."

TOUCH: Light and fluid but still a soft introduction into summer's warmth. We're talking linen, crinkled cottons and soft light tailorings layered with chunky fisherman knits for the slightly breezier evenings.

TASTE: Is preppy making a comeback? Are we entering a Nate Archibald-style era? It certainly seems that way, especially with the resurgence of mid-2000s trends popping up across the cultural landscape. From fashion to lifestyle, the influence of that clean-cut, polished preppy aesthetic is everywhere, signaling that this classic look might be on the verge of a major revival.

Click the gallery to see the whole collection.

For more NYFW runways, read about Willy Chavarria's SS25, "Welcome To América."

Click here to view full gallery at Hypebae