Tommy Hilfiger looks back on 25 years in fashion

"I really strive for all-American cool," says designer Tommy Hilfiger. (Sept. 12, 2010) Credit: Getty Images
He's rocked and he's rolled for more than 25 years.
Tommy Hilfiger is marking a quarter century of his namesake brand this fall, celebrating with a splashy show during Fashion Week, tailgate parties and anniversary products, but his career is, in fact, longer than that: He's had a fashion gig since high school, when he decided Elmira, N.Y., needed a denim store to keep up with the 1960s rock-star trends.
He opened People's Place, catering to the local college crowd and everyone headed to Woodstock. "I wanted to build a business around all this pop culture," says Hilfiger, who ticks off music, movies, celebrity and art as the long-term common threads in his signature look that has evolved through phases of hippie, preppy, Americana and glitzy influences.
"One of the most important things to me," Hilfiger says, "is to make things real, not have models who are perfectly groomed or clothes that are too perfect. It all has to have a twist, because that's how people live." Despite the success and fame he enjoys now, the 59-year-old designer comes across as a very normal guy - and that's a compliment.
Hilfiger certainly hasn't been immune to ups and downs. The brand has been bought and sold by investors with Phillips-Van Heusen Corp. as its current owner, while Hilfiger has creative control.
He has been criticized - alternately - for dabbling in too-fancy, high-price pieces and for going too casual with logo-covered looks. But that seems to have tempered since Hilfiger recommitted himself to clean, modern classics a few years ago.
"There have been a few incarnations of Tommy himself and his brand, but what's interesting now is he's firing on all cylinders," says Durand Guion, Macy's men's fashion director. "He's come into his own. The brand has its own appeal, particularly that it's an American brand with an American sensibility."
It's really all the good stuff, Hilfiger says. "I've learned not to take things so seriously around here. I'm using the 'F-word' a lot lately: fun - and that's what fashion is. Clothes are meant to be fun."
Tommy's tome
Tommy Hilfiger celebrates his world in a new ultra-luxe $550 book published by Assouline that is, essentially, Hilfiger's scrapbook. Scribbles in Hilfiger's handwriting explain his affinity for Steve McQueen, tartan plaid and tongue-in-cheek advertising. He has created collages that pay tribute to people, places and things that move the needle and generate buzz, but there also are personal moments - a family portrait of Hilfiger and his eight siblings, and a very Grace Kelly-esque photo of his wife, Dee. The book's available at shopassouline.com.