Andy Hilfiger sits by his desk at Artistix, a fashion company in the pulsating center of the grimy end of New York City’s clothing district near Eighth Avenue. Sketches and look books are strewn in front of him. A guitar hangs in the office, and the walls are covered by paintings by Greg Polisseni, an artist from Rochester, New York, who owns the company.
Hilfiger opens a digital file on his computer, and up pop styles from the Artistix women’s and men’s shows. Then he flips through an illustrated look book. It’s all about La La Anthony’s new collection, which debuts in spring 2017. The styles are very much like the actor and social media maven herself: cute, stylish, and accessible to the young and the youthful. (Anthony, one half of the celebrity power couple of which the other 50 percent is NBA star Carmelo Anthony, also has a higher-priced line called 5th and Mercer.)
Behind these two entertainment-meets-art-meets-fashion ventures is Andrew “Andy” Hilfiger, who has been adept at bringing celebrity and style together in the make-money fashion business. Anthony’s a good bet, he believes, because she has an engaged following of women for whom she’s a role model. “She’s a woman of empowerment,” he said. “It’s not like her five million followers are a bunch of guys just staring at her because she’s hot.”
The collection is slated to launch at Lord & Taylor and will be priced so millennials can buy it. These are the sorts of issues Hilfiger works through. And while he prefers to operate, as it were, behind the curtain, he has, in fact, been big brother Tommy’s secret weapon for years.
Tommy projects the kind of gravitas, restraint, and vision necessary to build a global billion-dollar fashion brand—with his own name on it, thank you. Andy, thickly built, with a ready smile and short tousled hair, is his brother’s alter ego: the loosey-goosey, charming, aw-shucks rocker who gave the brand an authentic pop culture dimension.
Tommy Hilfiger would be a powerhouse brand even without Andy. But whether the name would have become a cultural touchstone without his input—that’s questionable.
Andy’s forte is helping artistic types navigate the colorful waters of the business of fashion, the depths of which can be resolutely murky. As he put it, “It’s a lot of work. They’re always surprised how much it takes.” He’s guided Nicki Minaj when she created her lifestyle collection for Kmart, worked with Steven Tyler and Adam Levine, and collaborated with Jennifer Lopez on a joint fashion and fragrance line in a long-running partnership that ended in 2010.
“I know how much knowledge he brings to this area,” said Anthony. “He’s been integral to so many businesses. He gets it. He knows this world.”
It’s always helped that Hilfiger, 55, played guitar in one band or another, including with his late brother Billy, ever since he was in high school. “I’ll be at B.B. Kings in a couple weeks,” he said. He can understand the celebrities’ journey and they perhaps see in him a relatable spirit. But, he explained, while he’s cavorted with pop, rap, and jazz musicians, “the stuff I played was the rock and roll stuff” like Queen—like hair down his back and bangs covering his eyes. He takes his guitar off the wall and strums a few riffs from “Another One Bites the Dust.”
Polisseni values the Hilfiger combo of fashion savvy built on decades in the business and musical skills that have taught him all about “making something out of nothing, which is what I do as an artist,” he said.
It started with Formula One, Hilfiger explained. A few years after Tommy launched his company in the ’80s, he asked Andy to coordinate the dressing of race car drivers in his designs. “Then Tommy said, ‘I need you to go on tour with Peter Frampton.’ We couldn’t afford The Who, so we sponsored Peter Frampton and dressed him and his band.”
Shortly after that, he dressed a teenage newcomer named Britney Spears. “The day we did the photo shoot, her album shot to number one. It was Q Tip, Mark Ronson, all these people were in it,” he said.
After that, everyone started calling, including the rappers. Hilfiger had no problem giving or loaning them fashions. As far as he was concerned, they were musicians and hip hop was hot and getting hotter. But “no one would give them clothes,” he recalled. “I was like, come to me, come to me, I’ll give you free clothes.” His crescendo moment came when Snoop Dogg (not yet Snoop Lion) wore a Tommy Hilfiger top with the supersize logos that were popular then, so you couldn’t miss it, on Saturday Night Live. Almost immediately, the top sold out.
“After a while, celebrities just started coming to me,” he said. “I wanted to dress them, but all the artists started to wanna do their own collections. I’m sitting there going: Why don’t I do this?” He started his own company, Starbranding, with Tommy’s help, and began guiding celebrities in creating their own fashion brands. Occasionally, he’d still jump in to work with Tommy off and on.
He now focuses all his time on Polisseni, Anthony, and building his own home and fashion brand Andrew Charles, sold exclusively on Overstock.com. Said Polisseni recently, “the thing I absolutely love about Andy is, he has the ability to act like a real son of a bitch, given his experience and his large life, but he doesn’t. He’s very humble.”
In his Artistix office, Hilfiger is showing a crisp edition of Tommy Hilfiger’s new book with an inscription that has touched him. It reads: “Dear Andy, this is the first copy. It just so happens it came off the press on your birthday. There’s lots in the book about all the influence you had in building the brand. I’ll always be grateful. Love Tommy.”
Constance White is a fashion journalist and brand consultant who is passionate about all things fashion and women’s empowerment. A former reporter for The New York Times, style director of eBay and editor in chief of Essence, she is working on a book on style for Rizzoli.