Inside Tommy Hilfiger's 40-Year Reign Over Pop Fashion

A breezy Mumbai evening by the sea, around a massive dining table crafted to resemble a yacht and decked out in the signature colours of his eponymous brand, Tommy Hilfiger moves through a select gathering of actors, musicians, sportsmen, scribes, digital dons and socialites. It’s his tried, tasted, trusted and treasured playground. Since the inception of his brand four decades ago, pop culture has been the definitive driving force for Tommy Hilfiger. He’s been clear from the start: his brand would compete with the competition, not look like it. And having the pulse on pop culture gives him the edge.

It all began with his first love—Rock and Roll. Inspired by David Bowie, The Rolling Stones, and sundry rock bands of the ’70s and their style, Hilfiger embarked upon creating collections and communities around the music scene.

Over the years, what started as a cross-pollination of fashion and music, the Tommy Hilfiger brand has become a melting pot of cool—enmeshed in celebrity culture and bringing together tastemakers and trailblazers, idols and iconoclasts from diverse fields. Hilfiger has collaborated with numerous cultural stalwarts—be it George Lois (Noted ad man and Esquire’s venerated creative director who created iconic covers in the ’60s) to most recently, the F1 great Lewis Hamilton with whom he’s been crafting collections. Some others in Tommy’s top brass collaborator list include Snoop Dogg, Aaliyah, Britney Spears, Shawn Mendes, Zendaya, Naomi Campbell, Kate Moss and Gigi Hadid to name a few.

Tommy HilfigerPhoto by Nishanth Radhakrishnan

Till date, Tommy Hilfiger carefully observes the zeitgeist, the shifts in culture, and in turn shapes culture itself, making his brand remain highly relevant. Interestingly, in 2016, while sharing his experiences for Esquire’s signature ‘What I’ve Learnt’ series, Hilfiger asserted—“I never think, ‘We’ve made it.’”

Two decades later, in Mumbai, as he visits Indian shores to celebrate 40 years in the business and steer one of the most influential titles in global fashion, we ask him once again—

So, Mr Hilfiger, do you still not say — “We’ve made it”? 

Our biggest successes have always come from connecting our brand to pop culture in authentic ways. There have been defining moments—like in the ’90s when the hip-hop community embraced our bold colours, oversized silhouettes and playful spin on prep. Since then, as you must have seen, we’ve continued building meaningful partnerships with cultural pioneers who bring fresh energy and new perspectives to the brand.

Right now, I believe we’re at a powerful intersection of style and storytelling. Our partnership with F1: The Movie is a great example—merging fashion, film and motorsport into something that feels distinctly ‘of the moment’.

But no, I still wouldn’t say “we’ve made it.” If you start thinking that way, you stop evolving. I’m always focused on what’s next. That’s where the magic happens.

Let’s talk about change. Ancient Indian scripture guides us to be like water—freezing, evaporating or flowing, adapting to every terrain and circumstance. You’ve also always embraced change and moved with the times. Tell us about your connection to the idea of change, how do you move and manoeuvre the brand with the times?

That’s a great metaphor! It captures something I’ve always believed: staying adaptable is essential to staying relevant. From the beginning, I’ve built the brand with a mindset of evolution. We always stay true to our brand DNA while responding to the world around us. Whether it’s connecting with subcultures,  championing diverse voices in fashion, or embracing digital innovation early on, change has never been something to resist. That’s how we keep the Tommy Hilfiger spirit alive: by flowing with culture, not standing still.

Since inception, celebrity has been intrinsic to the Hilfiger DNA. It’s like you invented celebrity/influencer marketing way before it was a thing. The list of your pop culture collaborators is mighty vast. Tell us about this brilliance in the field of (as you call it)—‘fashiontainment’. What makes your brand tick and shine?

I’ve always believed that when you invite cultural innovators into your brand’s DNA, you end up with something that’s true to who you are, seen through a fresh lens. From the start, I’ve been inspired by pop culture. Andy Warhol was an early inspiration—the way he broke boundaries between art, celebrity and everyday life stuck with me.

What we call ‘fashiontainment’ is everywhere. Look at Formula 1—the drivers have become cultural icons, the grid is a runway and the spectacle itself is a global phenomenon. That blend of speed, style and star power is exactly where we like to be—at the centre of culture as it evolves.

Tommy HilfigerPhoto by Nishanth Radhakrishnan

You started off with menswear—with prep style. And then over the many years, we’ve seen the brand bring out so many diverse menswear collections. So, tell us about your point of view and philosophy around designing menswear. Where are we? And where do we go next?

My first Tommy Hilfiger collection was menswear. From day one, the goal was to reimagine classics—button-downs, chinos, blazers—with a fresh twist. By playing with proportion, colour and detail, we found a way to bridge tradition and innovation, creating a version of prep that felt relevant, and youthful. That spirit still drives our approach today.

Men’s style is in a really exciting place today. There’s a renewed appreciation for refined, versatile pieces that are thoughtfully designed. It’s about confidence in simplicity, with a big focus on the right fabrics and the perfect fit. Our current collections also reflect that—relaxed tailoring, clean silhouettes and modern essentials that feel elevated yet effortless.

Tommy Hilfiger and India—it’s been a successful synergy. With the brand now deeply woven into both market and mindset, how’s the ride been, and what’s ahead?

India has always held a special place in my heart. I first visited in the early ’80s, and working on factory floors became the best design school I could’ve asked for. What always struck me about Indian fashion is its ability to honour tradition while constantly evolving. That balance between heritage and reinvention mirrors our own philosophy— taking timeless style and giving it a modern twist.

Today, the energy coming out of India is incredible. There’s a new generation of creators and consumers who are global in mindset but deeply rooted in their own identity. That’s where I see huge opportunity—to keep growing with the country, not just as a market, but as a creative force. We’re looking at bringing exciting new collections to India, as well as creative collaborations and experiences that reflect that spirit—bold, vibrant, and uniquely Tommy.

On a personal note, what inspires you?

Vintage shops, fashion archives and the constant evolution of style—there’s always something new to discover. Travelling also fuels my creativity. Each place offers a unique perspective on design, craftsmanship and self-expression.

How do you stay clued in to what’s current?

I’m endlessly curious. Always exploring new cultures, as well as listening to my teams and kids.

What qualities do you value in a person?

Grit, determination and originality.

Is there anything you regret not doing?

I’m a relentless optimist—I don’t regret anything and am always looking forward, learning and building what’s next.

What’s your biggest hope for the future?

We’re always working towards a more inclusive fashion future.

What's next for you and your brand?

I hope our brand inspires the next generation to dream, be creative, take bold risks and redefine the future of fashion. On a personal note, I’m looking forward to a summer holiday with my family—a chance to unwind and recharge.

What piece of advice would you give to someone who dreams of building a global fashion empire one day?

Always lead with optimism, inclusivity and originality—those values are the foundation of everything we’ve done. Most importantly, stay curious and deeply connected to both the creative and the business sides of your brand—that balance is essential for lasting success and longevity.

Photographs: Nishanth Radhakrishnan

Style & Creative Direction: Vijendra Bhardwaj

Make up: Eshwar Log

Hair: Justine Rae Mellocastro

Fashion Team: Komal Shetty

Bookings & Production: Varun Shah

To read more stories from Esquire India's May-June 2025 issue, pick up a copy of the magazine from your nearest newspaper stand or bookstore. Or click here to subscribe to the magazine.