From selling bell-bottom jeans out of the backseat of his car while still in high school to 1,000 eponymous stores around the world—it’s been a wild ride for Tommy Hilfiger. As he celebrates the 25th anniversary of his label, the designer who put the posh in preppy talks about life lessons and his latest project, set to debut in October: the Icon Collection, a limited-edition, classics-driven group that takes its cue from those who continue to inspire Hilfiger every day.

What advice would you give the Tommy Hilfiger of 25 years ago?
“Make sure you enjoy every day, because it goes by quickly, and stay true to your roots, which is preppy, all-American sportswear.”

Which collections or pieces continue to resonate with you?
“I’m still proud of my first collection, in 1985, because I really designed it for myself. I’ve also enjoyed the collaborations: working with Keith Haring’s art on handbags and shoes; the Helena Christensen bag and the Carla Bruni bag, both of which were charity efforts for Breast Health International.”

What was the thinking behind launching the Icon Collection?
“I’m inspired by American icons, so for the anniversary it made sense to develop 25 limited-edition pieces that celebrate their classic style—James Dean wore a jean jacket and jeans better than anyone else, Jim Morrison wore incredible leather jeans, while Grace Kelly was as chic and sophisticated in chinos and a white blouse as she was in a silk gown. I also loved the idea of making the classics new, fresh and exciting.”

How has the industry changed most significantly for you?
“I think about the world now when I design collections or when we’re thinking about image or marketing. Spain likes bright colors, while in Chicago and New York they want darker colors and more fashion and sophistication. In the early years we were designing just for America; now we’re a global brand.”

After 25 years, what’s most fun about being Tommy Hilfiger?
“The fun part has never changed—that I never do the same thing every day. It could be a fashion show one day, launching a shoe collection the next, a fragrance launch, a store opening in Beijing, working with a celebrity or sponsoring a concert. Never a dull moment, and it’s been a fantastic journey.” usa.tommy.com

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