Tommy Hilfiger: Fashionable Americana

Tommy Hilfiger has a career spanning 25 years. From “classic with a twist” blue jeans, to oxford button downs, loyalty and promotion from hip hop royalty, and a current resounding “Meet the Hilfigers” ad campaign that is a 30 second feast in visual Americana: Hilfiger has seen the fashion world through a quarter century, and built a lifestyle empire.

So, although I am not a preppy with a twist die hard, I jumped at the opportunity, and hailed a cab to the Harvard Club, to see this man in action.
In an oak paneled room with paintings of distinguished alum watching over his shoulder, Hilfiger recapped his years in the business. Even in this distinguished environment I was completely lost in what seemed like a whirlwind fantasy of trial and error.


Hilfiger’s first forays into fashion were multiple and varied; including Chapter 11, the rise and fall of People’s Place, and an infamous billboard he describes as the only time he considered walking away. He bought Gap jeans, personalized them, and was picked up by Bloomingdale’s. Although this personal embellishment led to much success for the Bedazzler inventors, it did not a successful fashion company launch, quickly realized when he couldn’t fulfill the order.

meet the hilfigers

However, out of each misstep he managed to find a learning, perhaps not immediately, but thankfully for us, sometime in the 25 years i.e hire the best people who do what you don’t (he targeted accountants and lawyers.), and learn what people love to buy (in his case he found it to be classics with a twist.)And when faced with what to do next, he reinvented every single classic piece from his own closet to be the best version of what he wanted to wear- literally building an empire from personal passion, in my mind the best and most enjoyable method.


Although a mega success I was struck by his humility. Clearly acknowledging a Hong Kong swear factory owner who paid attention when he was begging for a credit line, and the current CEO who helped to navigate the recent recession. Okay I was also awe struck by Vince Camuto sitting two seats down the row.

Whether a fashion or business enthusiast, both, or neither, this evening with a token of classic Americana was inspiring and reassuring of the possibilities in front of us all. A pretty fantastic way to start the month!

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