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14 Lessons From Tommy Hilfiger

In this FRONTPAGE feature from the new issue of Highsnobiety Magazine, the fashion icon and master of preppy style Tommy Hilfiger imparts us with industry wisdom and excellent taste.

I don’t remember a time before Tommy Hilfiger.

After getting canned by Jordache, Hilfiger launched his eponymous brand in 1985. The Elmira, New York–born designer created an instantly recognizable world: modern American preppy classics done in simple primary colors.

When launching the brand, Hilfiger contracted art director George Lois, who created a legendary campaign. The artwork led with a concise, bold statement: “The 4 Great Designers for Men Are,” with a hangman-style design listing known legends Ralph Lauren, Perry Ellis, and Calvin Klein. It finished with Hilfiger, a name much less easy to guess at the time. It was a challenging stroke of brilliance that positioned Hilfiger as the leader of fashion’s third wave of designers. Moreover, the campaign sent people in droves to his first store on the Upper West Side of Manhattan.

Tommy Hilfiger also put music front and center before it was par for the course. He sponsored the tours of Britney Spears, The Rolling Stones, Sheryl Crow, and Lenny Kravitz. He put David Bowie and Beyoncé in campaigns. He let his interests and long-standing love of music drive the brand. It worked.

You probably already know about his success. According to The Business of Fashion, by 2004, revenue was in excess of $1.8 billion, and in 2012, the CDFA presented him with the Geoffrey Beene Lifetime Achievement Award. His clothes are now available in more than 100 countries. He has written a memoir, and is a father of five and stepfather of two. What Hilfiger figured out is that commerce is as important as creativity. Applying that approach has allowed him to create a global powerhouse that continues to thrive even as trends shift.

We recently spoke to the fashion legend, who seemed genuinely happy to talk about retail, preppy style, seeking out the best in everything, and building a brand.

On Working in Retail

“I think you learn about life working in retail, but in the fashion business you learn about what may be important if you’re ever going to develop your own collection. Most designers who don’t have that opportunity find it challenging to navigate to a successful point.”

On the Inspiration for His First Store

“I grew up dressing in a preppy way. Everybody in my school did. And then, towards my junior year, suddenly people started growing their hair a little bit longer, and rock music came about, and Woodstock happened. The Vietnam War was going on. There were protests. Everything changed. It was a dramatic revolution in politics and fashion. That’s what prompted me to go into business. I opened a jeans shop and sold bell-bottoms, fringe vests, and incense. It was about making cool clothes for people who wanted to be in the groove or part of the scene.”

On His Checklist for Great Clothing

“You have to have a great fit. You have to have excellent quality. You have to have the right colors. You have to have a style that is wearable and affordable. You could have the greatest item, but you won’t sell it if it doesn’t fit. You could also have something great-looking, but if the quality isn’t good, you won’t sell. You could also have something incredibly stylish and cool and relevant, but if it’s too expensive, you might sell one or two pieces.”

On Balancing Commerce and Creativity

“I learned along the way, after some financial difficulties, that you need to understand both. Because if you’re very creative, but you don’t have a business head or a great partner, you won’t make it. And if you’re a good business person, but you have no creativity, you’ll fail. You need both.”

On Family

“Family is everything. We have a big family now. We have seven children between us. It’s fun. It’s a lot of fun. We learn a lot from them.”

On the Power of His Logo

“When I started, I was told by many, many people to take that logo off the clothes, because nobody wants to wear logos. And if I listened to the buyers, for instance, I wouldn’t be in business today. They told me that their customers don’t like logos and would never buy anything with a logo. They begged me to take my logos off, and I wouldn’t do it. But then, when I blew the logos up and made them really big, buyers, retailers, and people inside my business said, ‘This is ridiculous. Don’t do it. People don’t want to be a billboard. People don’t want to wear big logos.’ I made a sample of a rugby shirt with a big logo and a big name on it, and I asked Bloomingdale’s to do me a favor. I said, ‘Look, I don’t have a sign in the department. Could you put this on a mannequin? You don’t have to selI it, I just want it as a sign, so people know that’s the Tommy Hilfiger department.’ They had so many requests for that shirt. People were begging for it. And then Snoop Dogg wore it on SNL and it was all over. We probably sold… I don’t know, a couple million of them.”

On the Marriage of Clothes and Culture

“I’m all about keeping connected to the culture. And I always want the brand to be connected to pop culture. I would say I’m a purveyor of social media, because I want to know what’s going on, whether we’re talking about skaters, rappers, influencers, artists, Hollywood stars, sports stars — when LeBron and the team get off the plane to walk into a stadium, it’s a fashion show.”

On Music

“I’ve always been connected to music, because music inspired me when I was starting my business 50 years ago. The musicians were the ones who were setting the trends. Onstage they were wearing the coolest clothes in the world, but you couldn’t go into a store and buy those clothes.”

On His Broad Range of Inspiration

“I’m very visual. So I really want to see what’s going on in the world. I’m always looking for the best restaurants and the best wine and the best places to go, wherever I am. I like going places and seeing how different people are doing things and living their lives. I like looking in retail stores, looking at other brands, and finding out what other designers are doing. I love home design. It’s all very inspiring to me. I’m into architecture, art, watches, cars, homes, boats, jets, helicopters… I like to know what people aspire to.”

On What He Looks for in a City

“Good weather. And at least some activity that might be interesting.”

On Embracing Technology

“People are working differently. They can work at home, they can work on the subway, they can work on their phones, they can work wherever they are. Years ago, we’d send the factory a sketch, they’d make a prototype, it’d be wrong, and we’d have to fix it. It would go back and forth like this five times and then, finally, you’d get it right. Now everything is 3D-designed and we’re making 3D skins, so when we send those to the factories, the factories come back with a garment that’s almost perfect.

“I’m very interested in the metaverse and avatars and where it’s going, because it is definitely moving very quickly. If you don’t keep up with it or stay a step ahead of it, if you fall behind, catching up is very difficult to do.”

On Writing a Book

“I wanted to do it before I forgot those stories or forgot people’s names. My mind is very alert now, and I didn’t want to get to a point where I was looking back, thinking, ‘I can’t remember what happened.’ There were so many things that have happened in my lifetime. I wanted to share it. It was a learning experience, but it was therapy in a way, because I went back and started thinking about my father and my family. I’m happy I did it. But now I could write other chapters.”

On Building a Brand

“You have to start with a great product. And then you have to market the hell out of it. However you do it, whether it’s social media or by other means. You have to get the clothes on the right people, and you have to show up in the right stores.”

On the Key to Success

“If you follow your passion, whether you’re a musician or an actor or an athlete, you can be successful.”

Head here to get a copy of the new issue of Highsnobiety Magazine.

  • WordsChris Black
  • PhotographyCourtesy of Tommy Hilfiger Archives
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