When Tommy Hilfiger began his eponymous brand in 1984, the goal was to build a style distinctly American. Reimagining the look of the Ivy League, Hilfiger wanted a visual signature that wasn’t rigid, that could bend and change over time. This was a goal not only achieved but transformed into an enduring legacy that’s traversed all facets of both fashion and culture. “I never wanted it to feel exclusive,” Hilfiger explains to V. “We wanted to open the doors to the world of prep and let people express themselves and make their own rules. That spirit of individuality and optimism has stayed with us ever since.”

Celebrating four decades of the brand, V spoke to Tommy Hilfiger about timelessness, creativity and rock and roll.

V MAGAZINE: When you first began the brand, what was your design philosophy?

TOMMY HILFIGER: When I started the brand, I was drawn to the classic codes of prep and Ivy League style, which I wanted to reimagine with a unique twist. I loved the structure and the heritage but also felt it needed to feel more relaxed and in tune with how people were living. So, we took those timeless pieces—polos, button-downs, chinos—and adjusted the fit, the color, the attitude. 

V: What were your first design inspirations? What still inspires you as a designer? 

TH: My biggest inspirations have always been found throughout pop culture. One of my first major interests was the style of musicians, like the Rolling Stones, whom I wanted to dress like. Art came into it as well. Spending time with Andy Warhol in the early ‘80s changed how I saw creativity, as he connected his work to so many worlds. He approached everything with curiosity and openness, and that stayed with me. Today, inspiration comes from staying connected to what’s happening around me. I pay attention to how people are mixing things, how culture is shifting, and what feels new and exciting. I’ve always believed you have to connect to the zeitgeist if you want to stay relevant.  

V: When you look back at your work over the last forty years, what is most surprising to you about how your design sensibilities have changed? What has stayed the same? 

TH: It’s not surprising, but I always find it interesting how much the context around clothes has changed. The way people wear things today is more fluid, more individual. That’s influenced how we design—there’s more flexibility in how pieces come together. What’s stayed consistent is the foundation. I still believe in timeless essentials and iconic American wardrobe pieces that people instinctively understand. From there, it’s about adjusting the details so they feel right for a new generation.   

V: How do you find something new to invigorate your creativity each season?  

TH: There are a few creative worlds we always return to. Collegiate style, sport, nautical, utility, outdoor recreation—they’ve been part of the brand from the beginning. Each one brings a different kind of energy, and revisiting them across seasons gives us a strong starting point. The challenge is always how to reinterpret them in a way that feels right for now. The exciting part is finding fresh perspectives and new contexts that bring these ideas to life again. Collaboration plays a huge role in that. Bringing new people into the process keeps the brand evolving and prevents it from ever feeling static. We’re seeing that right now with Travis Kelce. He has a clear sense of style and a real connection to the archive. Bringing him into our New York world for the Fall campaign and building a collection together for Spring 2027 has opened up new ways of looking at those heritage pieces. It’s an exciting, creative dialogue. Sport continues to be a major source of momentum for us as well. With Liverpool FC, we’re rethinking how players show up off the pitch through a full wardrobe approach. With the Cadillac Formula 1 Team, it’s about creating fanwear that lives beyond race day. And with the U.S. SailGP Team, we’re bringing a new perspective to sailing, connecting performance with lifestyle in a way that feels current. 

V: What has been your relationship to the cyclical nature of fashion, where what’s old is new again? How has that affected the way you’ve made work over the years and today?  

TH: I’ve always loved that fashion is cyclical. In some ways, it’s reassuring. It means the pieces that matter don’t disappear; they come back interpreted through a different cultural lens. The beauty of our brand is that prep is timeless, so each season we can give it a contemporary perspective. Recently, I’ve been happy to see there’s been a return to dressing up, which we’ve worked with by giving our collections a sense of easygoing sophistication. This reflects the refined yet relaxed spirit of our times.  

V: How do you balance maintaining your own design sensibility and keeping up with trends and cultural demand?  

TH: What’s most important is to stay grounded in your own point of view. If you lose that, the work starts to feel reactive. I keep an eye on what’s happening, but I don’t feel pressure to follow it directly. It’s more about understanding why something resonates and then deciding how it fits into our world. That balance is what keeps a brand evolving without losing itself.  

V: What do you still want Tommy Hilfiger to be after all these years? What do you want it to mean to people? 

TH: We want to continue doing what we’ve always believed in: staying optimistic; inspiring by fusing fashion with art, entertainment, music, and sports; and working with a welcoming spirit at our core. The brand will keep reimagining the codes of prep and encouraging people to dream big. That spirit is what has defined us, and it’s what I hope carries us forward. 

V: What does Modern Americana mean to you now?  

TH: Modern Americana is a cultural language — optimistic, confident, and always evolving.  

V: What are your goals for the brand moving forward? What is your dream for American design moving forward?  

TH: For the brand, it’s about continuing to build on what we’ve done for forty years—staying connected to culture, breaking convention with relentless optimism, and creating the iconic Prep Made Current wardrobe. For American design more broadly, I think the strength is in its openness. There’s room to reinterpret, to mix influences, to keep things evolving without losing identity. That’s what makes it exciting to be part of.

This story appears in the pages of V161: now available for purchase!

Photography Petros Kouiouris

Fashion Fani Polychroniou 

Models Kristin Drab (IMG), Tianna St. Louis (Elite), Beauty Thet Thinn (Elite), Mayowa Adagunduro (Elite), Yuyang Cai (Heroes), Mumin Jangani (Heroes), Max Tate (Heroes), Samuel Watson (NEXT), Sacha Bilal (Soul Artist Management)

Makeup Kevin Cheah (OPUS Beauty) using Armani Beauty

Hair Rachel Polycarpe (Forward Artists) using Pureology

Executive Producer Kevin Warner (WAK Creative)

Casting Goran Macura

Lighting Director Vasilios Smaragdas

Cinematographer David Barron

Lighting Technician Pablo Espinoza

Movement Director Marly Phillips Nicol

Prop Stylist Claire Vitto

Photo Assistants Beka Maglakelidze, Michael Alexander

Fashion Assistants Adlet Bermukhamedov, Julizza Vivas, Irene Crespo

Makeup Assistants Chloe Yang, Jack Titcomb

Hair Assistant Simone Bailey

Prop Assistants Noah Duarte, Ana Kalvo

Production Assistants Ailbhe Killalea, Juliet Lloyd, Tianyun Lan

Production Coordinator Drew Bosset

Location The Dominick