Tommy Hilfiger brought fashion, celebrity and a generous dose of New York nostalgia together for Spring 2027, transforming The Plaza Hotel into the glamorous home of “Plaza Prep.”
Anna Wintour Kenia Os

The front row carried almost as much personality as the runway. Your images capture Anna Wintour seated alongside another guest, setting the tone for a show where established fashion authority met a younger generation of cultural names.

Camila Cabello Bad Gyal

Camila Cabello was among the confirmed guests at The Plaza, joining a front row that also included JISOO, Kate Moss, Patrick Schwarzenegger and leading names from music and sport. The celebrity dressing echoed Hilfiger’s world beautifully: collegiate layers, flashes of red, crisp shirting and an effortless American ease.

Brooks Nader 001

Away from the front row, the mood continued with relaxed off-duty dressing. Your Brooks Nader portrait — cropped white polo and dark indigo denim — could sit here as a perfect visual transition into the collection itself.

Winnie Harlow TommyHill

Your Winnie Harlow image brings another burst of personality to the celebrity coverage, with the rich red cable knit reinforcing one of the strongest colours running through Hilfiger’s universe.

The Collection

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On the runway, Tommy’s familiar prep codes were pulled apart and put back together with confidence. Rugby dressing appeared elongated and body-skimming, while green, red, navy and yellow punched through the traditional palette. The collection mixed collegiate references with oversized proportions, tartan, Oxford stripes and reinvented chinos. 

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The softer side arrived through fluid cream dresses, styled unexpectedly with baseball caps and trainers. It was an interesting collision: something almost evening-like worn with the casual confidence of someone crossing Manhattan rather than stepping onto a red carpet.

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Elsewhere, proportions became deliberately relaxed. Oversized polos met sports shorts, long socks and two-tone sneakers, with structured handbags adding polish. Nothing felt overly styled.

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Menswear pushed the collegiate idea further. Colour-block rugby shirts, oversized logos, plaid shorts and sweeping trousers gave classic campus dressing a playful new scale.

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Some of the strongest moments came through colour. Brilliant red against white felt wonderfully clean, while yellow trousers, an emerald shirt and navy double-breasted blazer showed how confidently Hilfiger can move beyond his famous red, white and blue. The official collection notes describe this as a meeting of “uptown tradition and downtown cool” — an idea that runs throughout the show. 

With Gigi Hadid opening the runway, Romeo Beckham closing it and Slayyyter delivering the surprise finale, Plaza Prep became more than another seasonal presentation. 

It was Tommy Hilfiger doing what Tommy does best: taking American classics, loosening the rules and making prep feel fun again.

Words: Angela Gaote | Fashion Thirst
Images: Courtesy of Tommy Hilfiger