On this Flight of The Retail Pilot Ken speaks with LEGEND, Tommy Hilfiger, Principal Designer, Tommy Hilfiger Global.

Uplifting and inspiring consumers since 1985, Tommy Hilfiger has pioneered one of the world’s most recognized premium lifestyle brands. With Hilfiger’s vision and leadership as Principal Designer, his eponymous brand celebrates the essence of classic American style with a modern twist. Tommy Hilfiger offers premium quality and value to consumers worldwide under the TOMMY HILFIGER and TOMMY JEANS lifestyles, with a breadth of collections including men’s, women’s and kids’ sportswear, denim, accessories, and footwear.

Hilfiger’s career in fashion began when he was a high school student in 1969 — opening his first store, People’s Place, in his hometown of Elmira, New York. A decade later, he moved to Manhattan to pursue a career in fashion design, before launching his namesake brand with a single menswear collection. Since then, global retail sales of TOMMY HILFIGER products have grown to reach approximately $9.1 billion in 2022, powered by more than 16,000 associates worldwide — present in 100 countries and more than 2,000 retail stores, including its largest global flagship store at tommy.com.

Hilfiger has a longstanding passion for philanthropy and making the world a better place for future generations. Through the global TommyCares organization, the brand supports various international initiatives and charities like Save the Children, the World Wildlife Fund and Fashion Minority Alliance. Hilfiger currently sits on the Board of Next for Autism. Through the Tommy Hilfiger Fashion Frontier Challenge and People’s Place Program, the brand is also making strides in its ambitious vision to create fashion that Wastes Nothing and Welcomes All – which actively focuses on topics such as social and environmental sustainability, diversity, and inclusivity in fashion and beyond.

Diverse achievements in business and fashion have earned Hilfiger numerous distinguished awards including the CFDA’s prestigious Geoffrey Beene Lifetime Achievement Award in 2012, British GQ’s Design Legend of the Year in 2020, BFC’s Outstanding Achievement Award in 2021 and WWD's John B. Fairchild Honor for Lifetime Achievement in 2022. Hilfiger’s life and career have been chronicled in his memoir, American Dreamer, published in November 2016 — reflecting his experiences in the fashion industry from the last 35-plus years. Recounting his early childhood and formative years, it explores the setbacks, triumphs, and sheer determination that drove him to build a multi-billion-dollar global brand.

Key takeaways from this interview include:

Tommy Hilfiger's Background: Tommy Hilfiger began his journey in retail and design at a young age, starting his own business at 18 years old by opening a retail store -People’s Place - selling jeans in 1969. This venture eventually led him to designing and creating products for his stores, culminating in the establishment of his own brand.

Innovative Store Concepts: Hilfiger's early stores, particularly People's Place, were not just retail outlets but cultural hubs influenced by music and fashion. They offered a variety of products, hosted band practices, and provided an immersive experience for customers, aligning with the youth culture of the time.

Cultural Influences on Brand Identity: Hilfiger aimed to differentiate his brand from traditional preppy styles by infusing it with elements of music, particularly hip-hop, and embracing a more inclusive approach to fashion. This cultural fusion helped establish the personality of the Tommy Hilfiger brand.

Disruptive Advertising Strategy: The Hangman ad campaign, conceived by advertising executive George Lois, was a bold and disruptive move that garnered attention for the brand. Despite...