There’s a pretty good chance you’ve at some point made a purchase that was either directly or indirectly influenced by pioneering fashion designer Tommy Hilfiger. The 64-year-old visionary has left a rare legacy on the industry, with his clothing line becoming one of the most recognizable brands of the 1990s. Thanks to a diversification of styles and products in the 2000s, Hilfiger is still going strong.
He started the Tommy Hilfiger Corporation in 1985, focusing his line primarily on prep-friendly men’s sportswear inspired by traditional New England style. The brand later offered women’s clothing and luxury fragrances. Through it all, Hilfiger himself has been the consummate renaissance man—writing books, sponsoring concert tours and playing a central role in the 2005 CBS series The Cut.
There’s been plenty of change along the way. His company went public in 1992, was sold to Apax Partners for $1.6 billion in 2006 and sold again to Phillips-Van Heusen for $3 billion in 2010. The one constant has been success—and the uncanny attention to trends that tends to spawn it. Even after the corporate shuffling, Hilfiger remains the brand’s lead designer and continues to oversee creative operations.
Things might have taken a decidedly different turn had Hilfiger accepted one of the design assistant positions offered by the respectable likes of Calvin Klein and Perry Ellis. Instead, the New York native elected to pave his own path.
“[Waiting to form my own eponymous line] came from a desire to create something that wasn’t out there already,” Hilfiger wrote in 2010. “I was really in tune with the market—I knew what existed, and I wanted this to be different. Maybe it’s the small-town boy in me, but I’ve always loved the prep school look, traditional Ivy League, and the clothes that sailors and jocks wear.
“I wanted to take these familiar old things and give them a more laid-back attitude, to make them modern and cool… [With Tommy Hilfiger Corporation in 1985], finally, I felt like I was doing work that felt natural, that felt good. The brand we were building felt so honest, so true to who I am, that it didn’t feel like a struggle at all.”
Hilfiger’s objective was to reinvent the traditional and make it trendy. In retrospect, he managed to achieve just that.
“I recreated what a khaki pant was supposed to be, what a button-down Oxford shirt or a polo shirt or a V-neck sweater was supposed to be and made them relaxed, oversized, with all sorts of detail and a cool, nonchalant, hip factor that was so missing from these uptight, preppy clothes,” he recently told Wallpaper’s Julie L. Belcove. “If you looked at the type of people who were wearing these preppy clothes, their personality was as boring as the clothes. I wanted the cool crowd to wear the clothes.”
Fast-forward to 2016, and the fruits of Hilfiger’s entrepreneurial labor couldn’t be more evident—especially when one peeps his gorgeous penthouse in Manhattan’s Plaza Hotel. Belcove took a look inside, and the results are about what you’d expect from a fashion extraordinaire.
There’s an impressive collection of Warhols, and that’s no coincidence.
“Andy was at the epicenter of pop culture and putting together what I call FAME—F, A, M, E—fashion, art, music and entertainment,” Hilfiger told Belcove. “To me it was the beginning of pop culture in the world. There was a sense of humor behind it. There was a sense of excitement. It was bringing all these worlds together.”
In a similar way, Hilfiger has integrated a wide-ranging reflection of pop culture into his own brand, evolving with the times and often shaping those times. His crib is almost certainly a product of that supreme aesthetic acuity.