‘We are all dressing up more,’ says Tommy Hilfiger, as preppy returns

19 hours ago 3

The key trend for the coming seasons was announced on day two of New York Fashion Week by Tommy Hilfiger, the man who has tamed the zeitgeist for 40 years. Why bother with the rest of the week?

Instead of a specific handbag, print or jacket (oversized, cinched or cropped), Hilfiger – who launched his namesake brand in 1985 – says it’s an attitude.

Surrounded by next season’s looks in his Madison Avenue headquarters, Hilfiger says, “We are all dressing up more,” noting that “men in particular have been very casual” for the past five to seven years.

Tommy Hilfiger and his wife Dee Ocleppo at the Met Gala in May.

“The pendulum swings both ways. It’s one way for a certain amount of time and then the era shifts.”

Women are along for the ride and beginning to button up: “The women’s world is becoming a bit more sophisticated, a bit more feminine and a bit more grown up.”

In short, we will continue to be pushing the limits of preppy style for spring, summer and the coming winter.

Preppy dressing, which has evolved from the attire worn by US Ivy League students in the ’50s and ’60s, conveniently sits at the core of the Tommy Hilfiger DNA and helped push the brand’s second-quarter revenue for 2025 to $1.14 billion ($1.71 billion), up 4 per cent on the previous year.

Think varsity jackets, like the one Hilfiger wears during our interview, chinos, blazers, crew neck jumpers, loafers and striped ties. These were the staples from the beginning. Even in the days before launching Tommy Hilfiger, the designer was looking to the past.

“I was studying vintage clothes, studying clothes from the past, like workwear, Western wear, all sorts of American clothes just to get an idea of how they were made, how they fit, the colours, buttons, detail of fabric ...

Supermodel Kendall Jenner with Tommy Hilfiger at the Formula 1 Miami Grand Prix in May 2024.

“And then I wanted to set out to create something different. I wanted to be preppy, but cool and relaxed.”

The cool part was given a helping high-five on an episode of Saturday Night Live in 1994, when rapper Snoop Dog wore a striped Tommy Hilfiger rugby top. The segment helped make the preppy aesthetic more inclusive. The top sold out the next day and R&B artists who embraced the label pushed preppy style out of its WASP comfort zone.

Troubled music artist and designer Ye (Kanye West) acknowledged this seismic shift in fashion in a 2022 Instagram post: “Snoop wearing this Tommy Hilfiger Rugby was the most impactful marketing moment of my young life.”

For Hilfiger, it’s just one of many marketing moments. There was the precocious and prescient billboard in 1985, in the style of the hangman game, announcing: “The four greatest American designers for men”. The little known Hilfiger’s initials were placed alongside those of Calvin Klein, Ralph Lauren and Perry Ellis.

Since then, campaigns featuring Aaliyah, Kendall Jenner and Shawn Mendes have kept Hilfiger’s full name in the headlines. Most recently Superman’s Nicholas Hoult and enduring supermodel Claudia Schiffer appeared in a campaign for The Hilfiger Racing Club, where preppy style meets F1 racing.

Actor Nicholas Hoult and Claudia Schiffer in the Hilfiger Racing Club campaign from Tommy Hilfiger, where F1 meets preppy style.

It’s sport that seems to excite the man and the label the most today, with Hilfiger taking a break from the runway and skipping New York Fashion Week.

Instead, there has been the major announcement that the brand is sponsoring Cadillac’s new F1 team in 2026, having formerly worked with Mercedes-Benz, Ferrari and Team Lotus in 1991. It co-ordinates perfectly with the Hilfiger Racing Club, which this month was joined by K-Pop star Jisoo in a new string of advertisements.

“It’s a different type of excitement because sport is and always has been part of my world,” Hilfiger says. “Professional sport is becoming so incredibly dominant and powerful to the public.

“To be honest, we were there from the beginning,” Hilfiger says, in relation to the growing influence of fashion on F1. “There’s the excitement, the noise, the speed, the agility, the technology.”

It’s a rare moment of youthful enthusiasm from the incredibly polite and considered Hilfiger, who delivers his thoughts with the certainty of a Thomas or straight-forward approach of a Tom, rather than a Tommy.

When it comes to the name game, Tommy Hilfiger the man has to separate himself from the name above the door of countless stores and clothing items.

“There’s me and the brand, but I’m very critical of the brand. I’m always looking at what might be wrong so we can make it better.”

So how can the brand be better for the next 40 years?

“We want to be the most powerful lifestyle brand in the world,” he says. “We are one of the most powerful American designer brands in the world. But I’m never satisfied being where we are today.”

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