Tracing Tommy Hilfiger’s All-American Career

Tommy Hilfiger. Photo: Douglas Keeve

In 1985, a billboard in Times Square called Tommy Hilfiger “the next big thing in American fashion,” alongside ads for established brands like Ralph Lauren and Calvin Klein. Now, over 30 years later, the label has become a multibillion-dollar household name.

Hilfiger started his career as a scrappy entrepreneur and self-proclaimed dreamer. Originally known for modernizing quintessential button-downs and chinos, he has consistently taken a youthful approach to American classics — like this year, when he produced an Instagram-friendly capsule collection with Gigi Hadid that immediately sold out.

In his book American Dreamer: My Life in Fashion & Business, written with Peter Knobler, Hilfiger celebrates the brand’s history. Out today from Ballantine, the book chronicles never-before-told stories — everything from Hilfiger flunking his sophomore year of high school to dressing celebrities like Beyoncé and Britney Spears.

Click ahead for a preview.

Tommy Hilfiger Was Once the ‘Bad, Bad Boy’ of Fashion