Tommy Hilfiger entered fashion through retail rather than the atelier, cofounding a clothing and record shop called People’s Place in upstate New York in 1968 with $150 saved from a gas station job, eventually overseeing a chain of ten stores. After People’s Place filed for bankruptcy in 1977, he moved to New York City in 1979 to pursue design work, taking jobs across several labels including Jordache Jeans.

His apprenticeship in branded sportswear came in the early 1980s under Mohan Murjani, the Indian textile financier whose backing in 1985 produced the first signature collection of modernized button-down shirts, chinos, and other preppy staples, the rugby shirt, the oxford, the chino, and the navy blazer treated as a uniform rather than a costume.

The Tommy Hilfiger label launched in 1985 with a single menswear collection, brought to public attention by George Lois’ Times Square “hangman” billboard. Through the early 1990s the cut loosened into a baggier menswear silhouette, oversized logos appeared on rugbys, sweatshirts, and denim, and the clothes found a second audience in hip-hop.

Tommy Hilfiger carpenter jeans sold heavily, with the trademark flag displayed on the hammer loop. Where Ralph Lauren cast the WASP estate and Calvin Klein cast the downtown body, Hilfiger cast the rapper in a rugby shirt, and after Snoop Dogg wore a Hilfiger sweatshirt on Saturday Night Live, the stores sold out the next day, with Puffy and Coolio walking the runway; the CFDA named him Menswear Designer of the Year in 1995.

In 2006 he sold the company to Apax Partners for $1.6 billion, and Apax sold it on to Phillips-Van Heusen in 2010 for $3 billion. Since the PVH acquisition in 2010, Hilfiger has remained Principal Designer of the house, directing the global collections, and the CFDA’s Geoffrey Beene Lifetime Achievement Award followed in 2012, with the BFC’s Outstanding Achievement Award in 2021 and WWD’s John B. Fairchild Honor for Lifetime Achievement in 2022.

The spring and summer 2025 show, his second runway after a two-year hiatus, staged on a decommissioned Staten Island ferry at Pier 17, returned to the prep grammar of navy blazers, embroidered cardigans, and baseball caps, closed by a surprise Wu-Tang Clan performance. Forty years on from the Murjani debut, the argument of the work holds steady, an American sportswear vocabulary of red, white and navy, rugby stripes and the flag patch, kept in circulation by the same crossover between preppy uniform and street wardrobe that defined the 1990s.