Since 1985, when he founded his brand, Tommy Hilfiger has become globally renowned as a pioneer of classic American cool style. Inspired by the iconic pop culture, both he and his creations have been characterized over the years by an optimistic mood that breaks fashion stereotypes and pays homage to individuality.

Today, under the guidance and vision of Tommy Hilfiger as its principal designer, the name Tommy Hilfiger has become one of the most popular lifestyle brands worldwide. Apart from clothing, shoes, and accessories, it designs furniture and home goods, sharing its youthful spirit with enthusiasts across the globe.

Meeting the American designer for the second time in Mykonos, a place he adores, is an exciting prospect. This year, his trip is motivated by the opening of a new Tommy Hilfiger store on the cosmopolitan and always thrilling Island of the Winds. We chuckle as we reminisce about our last meeting that ended with dancing and wine by the waves. “The new store is located in the heart of Mykonos, the ultimate summer destination.”

He effortlessly blends nautical heritage with the magic of the Mediterranean, offering a harmonious fusion of classic American freshness and island tradition. He loves being amidst the white Cycladic houses and local shops. “This building has a long history, it’s of traditional architecture and represents everything I love here,” he says with his wife Dee, his guardian angel and companion in the fashion world, by his side.

The Aegean breeze inspires him to talk about the island he frequently visits: “I love the food the island offers; I’m a fan of Greek cuisine. I enjoy the energy of the place, the pleasant disposition of the people, the sea’s waters, and the white-washed alleys. I feel happy here,” he emphasizes enthusiastically and continues, “My family and I have always enjoyed the vibrancy and the stunning scenery of Mykonos.”

“We love exploring new locations, discovering new spots, and relaxing on the beautiful beaches. It is truly a place where we can unwind, have fun, and enjoy the most delicious and healthy Mediterranean cuisine,” he says. When asked what Greece means to him, he responds, “Your country holds a special place in my heart as a timeless destination rich in history, culture, and natural beauty.”

“The picturesque landscapes, ancient monuments, and vibrant cities are food for my creativity,” he says. And what about the Greek audience? “For me, the Greek people embodies warmth, passion, and a zest for life. The relaxed demeanor and smiles create a welcoming atmosphere wherever I go. I admire the strong cultural identity and the indomitable spirit that enriches every experience in this sunny country.”

Tommy Hilfiger was born in Elmira, a small town in upstate New York. The second of nine children, he grew up with a typical American upbringing of the 1960s. His career in fashion began while he was still a high school student in 1969, when he fell in love with the music and style of music stars.

With only $150 in his pocket, he bought 20 pairs of bell-bottom jeans, modified them, and returned to his town to sell them, using the trunk of his Volkswagen as his display case. This initiative was hugely successful. Soon, young Tommy opened his first store, People’s Place, where, as he often says, he sold “the style we couldn’t find in our small town.”

His memories from his childhood with his family in Elmira, New York, are among the most precious to him. “Our home was a place of good company, filled with laughter and love. I remember the summers playing outside with my siblings, forging lifelong bonds and nurturing a sense of unity that continues to inspire me to this day,” he says.

Do you remember the first collection you released? “Certainly!” he responds immediately. “The 1970s were an exciting period for me as that’s when I started my journey as a designer. I was heavily influenced by my music idols, with rock ‘n’ roll largely shaping my wardrobe. I loved denim. Those designs were essentially the foundation upon which my brand evolved. Many times, I look back and realize how far we’ve come.”

“What matters most to the tireless creator is ‘staying true to our roots. We work with contemporary ideas to offer a fresh perspective that resonates with a global audience, drawing inspiration from the distinctive codes of Classic American Cool that are synonymous with our brand.”

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“In our latest collection, I collaborated with longtime acquaintance Kendall Jenner. ‘Kendall treats friends as family. She radiates optimism and warmth not only through her style but also through the way she connects with people. I’ve known her and her family for years, and it’s been fascinating to watch her upward trajectory in the fashion world. She has a vitality and a determined positive outlook on life that continues to inspire me.”

Tommy and Dee Hilfiger met on the French Riviera. Married since 2008, they own homes in various parts of the world, although they prefer to reside in their paradise, Palm Springs, USA. Their mansion, as tasteful as Tommy Hilfiger’s creations, has been featured in the most selective interior design magazines and luxury publications.

“When commitments allow, they travel to distant destinations because, besides being successful entrepreneurs, they are also authentic citizens of the world. ‘I enjoy every moment spent with my family. I want to discover new destinations and remain active. I often play tennis, but you might also find me just relaxing at home.'”

Since his first marriage in 1980, Tommy Hilfiger has had four children, and with Dee, who already had two children, they had one more. “As a father, I try to be present, support, and participate in every aspect of my children’s lives. It is my priority to spend quality time with them, encourage their interests, and guide them whenever they need it.

“Being a father is a role I love, and I am committed to being the best version of a parent for my children,” he admits. Tommy Hilfiger is straightforward, open, with that characteristic American spontaneity. “Living in a family with seven children, you are certainly happy. With so many members, the family is scattered. Some are with us, others in New York, some in California. However, we cherish the happy occasions when we are all together.”

Our conversation concludes with a message from the famous designer to his audience in Greece: “The rich history, vibrant culture, and warm hospitality always leave me with the best impressions. I am grateful for the support and love you have shown to the Tommy Hilfiger brand all these years. Let’s continue to honor creativity, diversity, and unity together. I wish you all the best!”