Go big or go home: that’s been Tommy Hilfiger’s modus operandi since 1985, when the designer—then an unknown upstart—mounted a splashy billboard in Times Square declaring himself one of the “four great American designers” (Ralph Lauren, Calvin Klein and Perry Ellis were the other three). It was a ballsy move that stunned New York fashion players and made him famous overnight. “People went crazy,” Hilfiger told documentary filmmakers for the 2009 advertising flick Art & Copy. “All of 7th Avenue said, ‘Who does he think he is? He’s no designer. Ralph and Calvin have been working for years and years and years.’ I knew there would be only one way to prove the naysayers wrong and that would be to come out with amazing clothes.”
Today, no one would question Hilfiger’s design chops. His logo is a cultural icon, he’s cornered the market on prepster cool, and his extravagant runway presentations have become a highlight of New York Fashion Week—not only for his over-the-top theatrics and star-studded front row but also, increasingly, for his on-point collections. Last year, he staged a full-on Sgt. Pepper tribute, complete with a grass carpet, a field’s worth of gerbera daisies and a parade of flower-power frocks. For fall ’15, it was a Friday Night Lights–worthy spectacle that saw Gigi Hadid and Binx Walton stomp down the massive football-field-turned-catwalk wearing the current cool-girl dress code: varsity stripes, athletic jumpers and flippy cheerleader skirts.
In many ways, the Tommy Hilfiger origin story reads like an American dream come true (in fact, he’s currently working on a memoir, slated for release in 2016). The designer, who was born in upstate New York (a.k.a. the birthplace of preppy style) and has no formal fashion training, got his start selling bell-bottoms out of the trunk of his car. When he was 18, he opened People’s Place, a groovy boutique that carried leather jackets, records, incense and customized jeans. It was the early ’70s and he was obsessed with rock ’n’ roll: “Woodstock had just taken place and it was all about the Rolling Stones, The Beatles, The Who, Jimi Hendrix, The Doors, Janis Joplin,” he recalls wistfully in a phone interview. “You could rarely find what they were wearing onstage in stores, so I developed my own style.” This soon-to-be-signature look blended the collegial vibe of his hometown with the music, art and flash of his pop-culture fantasies. To this day, the Tommy Hilfiger aesthetic remains bound up in the style of MTV icons: everyone from Michael Jackson to Britney Spears to Nicki Minaj has had a Tommy moment. “Pop culture influences fashion, fashion influences pop culture, music influences fashion, fashion influences music,” says Hilfiger. “It’s never any one way, and that’s what makes it interesting.”
The brand hit its stride in the early ’90s, when its street cred dovetailed with the explosion of hip hop. It was the height of logomania, and Hilfiger fed the hype with exactly the kind of bold, in-your-face branded gear that teenagers were craving. The tipping point came in 1994, when Snoop Dogg wore a Tommy rugby shirt on Saturday Night Live. Sales reportedly skyrocketed by $90 million that year, and Tommy’s red-white-and-blue insignia became an instant status symbol. For his part, Hilfiger embraced the boom, enlisting Coolio, Method Man and Sean “Puff Daddy” Combs to walk in his fall ’96 runway show. “We were leading the way with trends for young people,” says Hilfiger. “No other designers were doing anything athletic-oriented. I was on my own, and then everyone started doing it.” And when everyone starts doing it, it’s not long before your 15 minutes is up. “It became, let’s say, obsolete at the end of the ’90s,” says Hilfiger, who ended up selling his company to a private investment firm in 2006, due in large part to declining sales (he stayed on as principal designer).
But with fashion currently in full-on retro redux mode, the logo legends of that decade—Polo, DKNY, CK and especially Tommy Hilfiger—have become hot commodities on the vintage scene. “The brand is our bestseller right now,” says Jesse Heifetz, owner of F As In Frank Vintage in Toronto and Vancouver. In fact, he says the most searched term on the store’s website is “Tommy Hilfiger vintage,” which might explain why its Instagram feed is a veritable hit list of boldly stamped jackets, tees, jeans, overalls and caps. According to Heifetz, collectors of vintage TH pieces fall into two camps: “There are the purists, who want to look like they literally stepped out of 1992, and then there are people who are just looking for a hat or a rugby shirt to incorporate with current trends,” he explains. “Either way, it’s not going anywhere any time soon.”
Most of Heifetz’s customers aren’t old enough to have lived through the original Tommy craze, but you would never know it looking at the trendster cycling by in a conspicuously branded backpack or the hipster babe sporting an oversized logo tee as a dress with Cons. Clearly, the second time around can be just as sweet as the first. “Fashion is cyclical,” says Hilfiger. “If something goes out of style, the chances of it coming back in are very high—it just depends on when.”
Double Take: New-school celebs are rocking old-school red, white and blue, and giving us a serious case of the deja vus. Click through the gallery below to see our favourite looks from then and now.
Aaliyah stars in Hilfiger’s 1997 ad campaign.