Tommy Hilfiger Enters New Era of Prep at New York Fashion Week

Uptown polish met downtown cool as Tommy Hilfiger took over one of New York’s most iconic addresses for Spring 2027.

For Spring 2027, Tommy Hilfiger checked into The Plaza Hotel and naturally, brought New York Fashion Week along for the ride.

Dubbed “Plaza Prep,” the collection saw Hilfiger return to an address with personal significance; the designer once lived at the legendary hotel with his family. This time, its Palm Court and Terrace Room became the backdrop for a playful reimagining of the brand’s signature American prep.

“For 40 years, I've been inspired by the style of New Yorkers, how the people of the city take the classics and make them their own,” Hilfiger says. “This season, The Plaza is our playground, where Tommy icons feel remixed and refined for today.”

And remixed they were.

The familiar red, white and blue remained, but flashes of vivid yellow and green brought a new energy to the palette. Rugby dresses arrived colour-blocked, Oxford shirts were rendered in Ithaca stripes and traditional tartan found its way onto blazers and Ivy jackets. Polos played with proportion, some shrunken, others deliberately oversized, while chinos were cut into high-rise hot shorts or reconstructed with denim-inspired twisted seams.

Elsewhere, the Tommy flag appeared faded and washed across superfine suede, silk-cashmere and oversized totes. Underfoot, the mood leaned distinctly nostalgic, with rounded ’90s-style skate sneakers joining boat shoes, penny loafers and leather pool slides.

It was prep, certainly, but with its tie loosened.

The Plaza Guest List

Of course, a show at The Plaza requires an equally impressive guest list.

Gigi Hadid opened the runway, while Romeo Beckham closed the show, bringing a relaxed edge to its polished final look.

Watching from the front row were Kate Moss, Camila Cabello, JISOO, Patrick Schwarzenegger, Arón Piper and Carmelo Anthony, alongside basketball stars Josh Hart, Karl-Anthony Towns and Miles McBride and a mix of personalities spanning fashion, music, entertainment and sport.

After four decades of reshaping American classics, Hilfiger’s latest chapter feels less about reinventing the uniform entirely and more about remembering what made it fun in the first place.

At The Plaza, prep has officially checked back in.