Hilfiger grew up as the second oldest of nine children in an Irish Catholic family in Elmira, a small town near Cornell University. His father was a watchmaker and his mother was a nurse. In 1969, Tommy Hilfiger bought jeans for $150 that he sold to local youth. The deal was completed quickly. Buoyed by the success of this campaign, he initially continued on this basis. With the saved profits, Hilfiger opened his first store in 1969, which he called the "People Store". There he offered young fashion for students. The business flourished and further branches were opened. In a short time, Hilfiger was the entrepreneur of a total of ten fashion stores. With the increased sales of the items, he had pants produced with his own label from the mid-1970s.

In 1979 he sold his chain to devote himself full-time to fashion design. He took the step of becoming self-employed as a fashion designer, even though he had never completed any fashion training. In 1984 he presented his first own collection - sporty clothing in a classic American look. Since then, this stylistic language has shaped Hilfiger's fashionable designs; it has also been referred to as "casual wear". His target group was made up accordingly: young people who live out their fun in life. His preferred colors also became all-American: the white, blue and red of the US national flag. His clothes were adorned with his own Hilfiger label. Sportiness, youth and lifestyle became the keywords that he used to promote his collections.

In the 1980s, Hilfiger fashion appealed primarily to middle-class Americans. At the same time, the enthusiasm spread to young African Americans, who were included in the target group advertising. From the 1990s onwards, the American fashion designer based his style on the college look of the east coast of his country, which he changed to a sporty look. The "Hilfiger" brand already had sales of $25 million in 1990. In 1992, Hilfiger took his company public. In 1995, the fashion designer was named Designer of the Year for men's fashion. In addition to the Fifi Award, he received other awards that document the success of Hilfiger's designs. Hilfiger has long been one of the prominent and important fashion designers. In 2000, his company achieved sales of around $200 million.

Collections for women, men and children followed, including tailored suits, underwear and comfortable sportswear. His patriotic look was also distributed in Europe and Germany. In addition, he had opened a new product line with accessories such as watches, which became increasingly important. Hilfiger sold his company to the investment firm Apax Partners for $1.6 billion in 2005. On December 12, 2008, he married former model, Dee Ocleppo. Together they became parents to a son, Sebastian Thomas. From his first marriage to Susie, Hilfiger was already the father of four more children, Alexandria, Richard, Elizabeth and Kathleen. In March 2010, the fashion group Hilfiger was taken over by Phillips-Van Heusen for the equivalent of 2.2 billion euros.