When Tommy Hilfiger opened his first store, People’s Place, in his hometown of Elmira, New York, he had $150 in savings from working nights at a gas station and a dream larger than life. At People’s Place, he and his buddy sold bellbottom jeans to their community of friends. “I wanted it to be a place for people who loved fashion and music,” he recalls. That dual passion for style and culture would later define his eponymous brand, launched in 1985.

Hilfiger’s ability to blend classic Americana with contemporary cool set him apart as he drew inspiration from timeless military styles like the peacoat while pushing boundaries with bold cultural collaborations. One of the most iconic moments in his career came in 1996, when he hosted a groundbreaking runway show at London’s Natural History Museum. With Naughty by Nature performing and supermodels Naomi Campbell and Kate Moss walking the runway alongside actress Joy Bryant, the event introduced Europe to what Hilfiger describes as “America’s culture at its best.”

Aaliyah’s effortless style further cemented his brand as a ’90s streetwear staple. Introduced to Hilfiger by stylist Kidada Jones, Aaliyah embodied the Tommy Hilfiger ethos, blending oversized silhouettes with sophistication. Today, her influence remains as timeless as her look.

Pop culture remains a driving force in Hilfiger’s work, inspired by icons like Andy Warhol—whom Hilfiger calls a friend—and musical legends from Bob Dylan to Wu-Tang Clan, who reunited with the brand for a 2024 runway show.

Despite his global success, Hilfiger’s tastes remain surprisingly grounded. His favorite color is blue, his go-to wardrobe staple is the navy blazer in every possible variation, and his indulgence is Indian food, enjoyed sparingly. His hidden talent? Making his family laugh with imitations and voices. “Yes, my kids think it’s funny,” he admits with a chuckle. When asked about a fashion moment he would hope would return he has no hesitation as he says, the 70s.

Through it all, Hilfiger’s philosophy is simple: “Never give up.” It’s a mantra that propelled him from his first store in upstate New York to runways worldwide, redefining modern Americana and being what he calls “fresh and familiar.” With an enduring legacy shaped by passion, innovation, and a knack for storytelling, Tommy Hilfiger continues to stitch his name into the fabric of fashion history.

From Elmira, New York, to shaping a global brand, what aspects of your small-town upbringing influenced your vision for creating an accessible, all-American lifestyle in fashion?

Growing up in Elmira, New York, I was always inspired by the vibrancy and energy of New York City. Traveling there as a teenager, I remember being captivated by the fashion and the excitement—the pulse of the city was intoxicating. It opened my eyes to a broader world of style and culture, which fueled my ambition to create something accessible for everyone, regardless of where they came from.

From the very beginning, I envisioned Tommy Hilfiger as a brand that was wearable, relatable, and affordable, catering to a wide audience. I wanted it to be something people could see themselves in, a reflection of the all-American spirit. That vision hasn’t changed. Now, forty years later, we call it “premium” or “affordable luxury,” but at its core, it’s always been about offering high-quality, stylish clothing that’s accessible to many. Accessibility was — and still is — at the heart of my philosophy. 

Was there a specific moment or experience early in your career when you realized that the Tommy Hilfiger brand could become a defining force in American fashion?

From the very beginning, I dreamed of building a brand that would not only define but also celebrate American fashion. That dream has always been my guiding light, my north star. I’ve been fortunate to work with an incredible team who shares that vision, and together we’ve built a global lifestyle brand that continues to evolve.

Tommy Hilfiger the brand is synonymous with America. How have you managed to stay relevant in a rapidly changing industry while balancing heritage and creativity?

The key is never letting go of the DNA of the brand—its essence and heritage—but always modernizing it. It’s about staying true to the core of what makes Tommy Hilfiger iconic while evolving to remain relevant. For me, that relevance comes through what I call “F.A.M.E.S.”—fashion, art, music, entertainment, and sports. These cultural intersections have always been central to the brand.

I learned a lot about this from my friend Andy Warhol. He immersed himself in pop culture and made it the subject of his art, painting the people and icons at the forefront of the zeitgeist—musicians, Hollywood stars, and cultural disruptors. That approach resonated with me, and I connected Tommy Hilfiger to the same ethos, ensuring the brand remains entwined with the cultural fabric of its time. Being disruptive in marketing is also crucial. Without it, you risk becoming just another brand.

How did Aaliyah become a part of the brand?

It all started with Kidada Jones, Quincy Jones’s daughter, who was working for me as a stylist at the time. She introduced me to Aaliyah, who immediately connected with the brand. Aaliyah loved the clothing—she had this effortless way of making it her own.

My brother, Andy, had the brilliant idea of featuring her in one of our advertising campaigns. We paired her with Mark Ronson, and the result was pure magic. From that moment, she became part of the Tommy Hilfiger family. Her style—the way she wore oversized pieces with a blend of street and sophistication—redefined how people saw our clothes. What’s remarkable is how her look remains so timeless. The way she styled herself continues to influence fashion today.

We often hear about the triumphs, but can you share a pivotal challenge or failure in your journey that shaped your perspective on the business of fashion?

One of the most transformative moments in my career was when the hip-hop community embraced my brand. Seeing these artists and kids wearing my clothing taught me something invaluable: fashion isn’t dictated from the top down—it comes from the streets, from the culture. It wasn’t without its challenges, but it was also one of the greatest lessons I’ve ever learned.

I wasn’t the only designer noticing this shift, but I was one of the few who truly embraced it. I didn’t just admire the influence of hip-hop—I invited it in. Artists came into our design studio, looked over sketches, and gave us feedback. They told us what they liked, what they didn’t, and what needed to change. It was about collaborating. These weren’t just partnerships; they were moments of creative exchange that shaped the evolution of the brand.

Musicians and producers became integral to our identity. I’ll never forget when Beyoncé performed at one of our fashion shows with Destiny’s Child—when she was sixteen. Iman and David Bowie, music and fashion royalty, appeared together in one of our ad campaigns in the early 2000s. These moments solidified a connection between music, culture, and fashion that became central to the Tommy Hilfiger ethos.

You’ve collaborated with cultural icons ranging from music to sports. If you could collaborate with one figure—past or present—who would it be, and why?

I don’t know just yet because I’m always thinking about the future. That forward-thinking mindset has guided our collaborations. Take Zendaya, for instance—she’s become one of the most important fashion icons in the world today, but we partnered with her just before she ascended into that stratosphere. It was the same with Gigi Hadid and Lewis Hamilton. When we began working with Lewis, he was already a recognized athlete, but not at the mega global celebrity status he holds now.

What I’ve learned is that it’s not just about finding someone famous—it’s about identifying “the next.” It requires thoughtfulness, analysis, and a deep respect for the individual. It’s essential that our collaborators not only fit the brand’s ethos but also truly respect and love it. It’s never just about paying someone to represent us; it’s about building a meaningful partnership rooted in authenticity.

If you could go back and give advice to the young Tommy Hilfiger sketching designs in your basement, what would you say that goes beyond the usual “stay persistent” mantra?

I’d tell my younger self, “Expanding into Europe will be one of the best decisions we ever make.” Until then, we were rooted in America, but entering the European market opened my eyes to how our designs could resonate on a global scale. One of our partners, who had a deep understanding of the European market, urged us to expand. Following that advice, we held a fashion show at the Natural History Museum in London in September 1996, presenting our Spring/Summer 1997 collection. It was a groundbreaking event. Naughty By Nature performed live while Naomi Campbell and Kate Moss walked the runway alongside actress Joy Bryant. It was a collision of music, fashion, and culture that no one in Europe had ever seen before.

That moment was transformative. It wasn’t just about showcasing the clothes—it was about exporting “America’s culture at its best” to an entirely new audience. If I could go back, I’d remind myself to take those leaps and trust the right advice.

Sustainability is shaping the future of fashion. How do you envision the Tommy Hilfiger brand evolving in this area.

Our work in sustainability began more than a decade ago. Being in the denim business for so long gave us an early start, as many denim manufacturers recognized early on that sustainability would become critical — not just for the industry, but for the world. That foresight allowed us to integrate sustainable practices into our operations and we have made significant strides in the years since. As we move forward, sustainability remains a top priority. We’re scaling the use of recycled and regenerative materials, building circular business models like resale and trade-in, and continuing to explore innovative ways to minimize our environmental impact.

As someone who’s been in the industry for decades, what do you believe is still misunderstood about American fashion on a global scale, and how do you see the industry shifting in the next 10 years?

I think there’s a perception—especially within the industry—that American fashion is very commercial. And you know what? They’re absolutely right. American fashion is commercial, and that’s precisely what gives us the edge. It’s what fuels our financial success, allowing us to produce incredible fashion shows, launch bold advertising campaigns, hire the right talent, and build iconic stores. That commercial success is our strength—it gives us muscle and reach.

I’ve never aspired to create clothes that are destined to be one-offs or museum pieces. I want to create clothing that people actually wear, that becomes part of their lives. That’s what makes American fashion relatable and, frankly, powerful.