[8] Tommy Hilfiger's career in fashion began in 1968, when he cofounded a clothing and record store named People's Place in upstate New York.

[9] In 1979, Hilfiger moved to New York City to pursue a career as a fashion designer,[11] working on several different labels including Jordache Jeans.

With Murjani's backing[10] in 1985, Hilfiger debuted his first signature collection,[4] which featured modernized versions of button-down shirts, chinos, and other classic preppy styles.

[3] The new clothing line made its debut with a high-profile marketing campaign, which included a large billboard in Times Square[4] by advertiser George Lois.

[10] Throughout the 1990s, the company's marketing division worked in tandem with the popular music industry, and as early as 1993 Hilfiger was an official sponsor for Pete Townshend's Psychoderelict tour.

[17] As roomier styles with oversized logos became popular with hip-hop artists in the mid-to-late 1990s,[18] Hilfiger's style of clothing became both increasingly popular with the American "preppy" scene and as hip hop fashion,[4] and when Snoop Dogg wore a Hilfiger sweatshirt during an appearance on Saturday Night Live in the 1990s; it sold out of New York City stores the next day.

Hilfiger courted the new hip hop market, and rappers like Puff Daddy and Coolio attended his runway shows.

Gehring and Hilfiger narrowed their focus in the United States to the profitable core sportswear line, and U.S. sales began to rise in 2010.

[33] In January 2015, Tommy Hilfiger debuted a digital sales showroom at its New York City headquarters, which the publication WGSN opined would "transform the traditional buying process.

[8] In the late 1990s, Tommy Hilfiger and other large American textile companies such as Calvin Klein and Sears were defendants in a class-action lawsuit alleging that luxury clothes were being manufactured in sweatshop conditions in Saipan.

After a group settlement that admitted no liability, in March 2000, Tommy Hilfiger volunteered to allow independent oversight of their manufacturing on the island.

"[44] Tommy Hilfiger later signed a Bangladeshi safety accord along with eighty other Western retailers, with the goal of protecting unionizers.

[45] In 2014, PVH was consulting about investing in Ethiopia in relation to Tommy Hilfiger and Calvin Klein, with labor rights among the key talking points.

[47] Research accuses Hilfiger receiving and distributing products out of Chinese forced labour camps for Uyghur people.

[48] In 1985, to help him launch his first collection, Hilfiger hired advertiser and graphic designer George Lois[13] to make a billboard for the center of Times Square in New York City.

[4] Instead of models, the ad featured the initials of three well-known fashion designers—"PE" (Perry Ellis), "RL" (Ralph Lauren), "CK" (Calvin Klein), and announced that "TH" (Tommy Hilfiger) was the next great menswear designer.

The brand created the publicity tour "Prep World" in 2011, which featured specialty pop-up shops in Paris, New York, London, Stockholm, Los Angeles, Madrid, Milan, the German island Sylt, and the Belgian town of Knokke.

Hilfiger made personal appearances with author and preppy expert Lisa Birnbach, as well as designing a special clothing collection to support the initiative.