The Tommy Hilfiger Footwear collection remains true to Tommy's design philosophy of "Fresh American Style." Tommy Hilfiger Footwear offers a modern twist to classic footwear designs with great colors, unique details, and high quality fabrications and materials. Their contemporary interpretation of classic styles has increased the popular interest in men’s casual shoes, men’s training shoes, men’s running shoes, and men’s outdoor shoes. The Tommy Hilfiger women’s shoe collection offers a wide selection of women’s contemporary shoes including women’s casual shoes, women’s athletic shoes, and women’s canvas shoes.

In 1969, while still in high school, he began his retail career with $150 and 20 pairs of bell-bottom jeans. Soon after, he opened his own small chain of stores called People’s Place. Self taught, he began designing the clothes that his customers wanted but could not find.

Tommy Hilfiger grew up in an Irish Catholic family, the second of nine children. He attended Elmira Free Academy for high school. Rather than furthering his education, he started to work in retail at the age of 18. Hilfiger would trek down to New York City to get his hands on jeans and bell-bottom pants which he customized and resold at a local downtown Elmira, New York store, Brown's.

He later opened his own store, named The People's Place, around the block in downtown Elmira. The store was a hot spot for teens with frequent contests and live DJ appearances. Soon after, he opened his own small chain of stores called People’s Place. Self taught, he began designing the clothes that his customers wanted but could not find. Hilfiger moved to New York City, although he was offered design assistant positions with designers Calvin Klein and Perry Ellis, he turned them both down with greater plans in mind.

In 1984, he founded the Tommy Hilfiger Corporation, which went public in 1992, introducing his signature menswear collection. The fashion industry has bestowed numerous honors on Hilfiger. In 1998, Parsons School of Design in New York City honored him with their Designer of the Year award, as did GQ magazine for their annual “Men of the Year” issue. In 1995 he was named Menswear Designer of the Year by the Council of Fashion Designers of America (CFDA). That same year, he received VH1’s “From the Catwalk to the Sidewalk” award at their annual Fashion and Music Awards. He has also won several FiFi Awards, the fragrance industry’s most illustrious honor. In November of 2002, he was selected as GQ magazine’s International Designer of the Year award recipient in Germany. That same month, the Drug Abuse Resistance Education (D.A.R.E.) organization presented Hilfiger with the Future of America Award, D.A.R.E.’s highest honor, for his philanthropic efforts for America’s youth.

In August 2005 Hilfiger announced he was selling his company and, before the year ended, it was purchased by Apax Partners.