He’s rocked and he’s rolled—and Tommy Hilfiger has done it for more than 25 years. Hilfiger is marking 25 years 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.