Hilfiger was born on March 24, 1951, in Elmira, New York, the second of nine children. Both of his parents were practicing Catholics. His father Richard was a watchmaker of German-Swiss descent and his mother Virginia (née Gerrity) was a nurse of Irish descent. Hilfiger also claims direct descent from Gilbert Burns, brother of the Scottish poet Robert Burns. Hilfiger has described his upbringing as very happy. He credits his parents with instilling a good work ethic and compassion for others. Hilfiger had an early interest in sports, fashion, and the music industry, a trend that ran in his family. One of his brothers, Andy Hilfiger, went on to work as a musician and designer, while Hilfiger’s other brother Billy Hilfiger would join King Flux as a guitarist.

Hilfiger spent the summer of 1969 working in a clothing store on Cape Cod, and afterwards he decided to use his life savings of $150 to open a clothing store in 1971 as People’s Place. The first store was located in downtown Elmira in what is now the site of First Arena and had a hair salon, a record shop, and rock concerts in the basement. To stock the store, Hilfiger and a friend drove to New York City to buy clothing such as bell-bottoms, peasant blouses, and leather jackets. Unsatisfied with this, he began sketching his own designs, and would later write that “designing made me happier than anything I’d ever done. I knew from that early work that designing would be my life.”

Hilfiger graduated from the Elmira Free Academy high school in 1975. His parents wanted him to get a college education and pursue a traditional career, and for a time he attended GST BOCES Bush Campus in Elmira.

In 1976 Hilfiger met Susan Cirona, an employee at the People’s Place in Ithaca; they married in 1980. Together they had four children: one son and three daughters. In 2003 Hilfiger’s daughter Ally was part of the MTV reality series Rich Girls. His son, Richard (“Ricky Hil”), is a musician. The Hilfigers divorced in 2000.

The People’s Place went bankrupt in 1977. Hilfiger enrolled in classes on commerce and the business side of the fashion industry. After then moving to New York City and working for several different labels, he set up a company called Tommy Hill in 1979. One of his first clients was Jordache Jeans, and as Hilfiger’s company expanded beyond denim, he spent time in India, learning more about his trade: “I would sit in the factory with my pile of sketches and watch them being made, tweaking as I went. There’s no better design school in the world.” In 1981 he founded the company 20th Century Survival, and the following year he founded Click Point, which designed women’s clothing.

In 1984, Hilfiger was approached by businessman Mohan Murjani, to pursue his goal of designing and heading a men’s sportswear line. Murjani backed the necessary investment for Hilfiger to establish his own brand. Later Hilfiger oversaw the design of the Coca-Cola clothing line for Murjani.

In 1985, he founded the Tommy Hilfiger Corporation with support from The Murjani Group. The new clothing line made its debut with a high-profile marketing campaign, for example setting up a large billboard in Times Square designed by George Lois. Hilfiger left Murjani International in 1989, with Silas Chou instead providing financial backing to the Hilfiger brand, and former executives of Ralph Lauren brought on board as executives of the newly formed company Tommy Hilfiger, Inc. The Tommy Hilfiger Corporation went public in 1992, introducing Hilfiger’s signature menswear collection. Hilfiger was named Menswear Designer of the Year by the Council of Fashion Designers of America in 1995. After licensing Pepe Jeans USA in 1995, in 1996, Tommy Hilfiger Inc. began distributing women’s clothing. By the end of the next year Hilfiger had opened his first store in Beverly Hills, which was followed by a store in London in 1998. Hilfiger was serving as the company’s co-chairman by 1997, and that year he published his first book, titled All American: A Style Book.

In 1995 Hilfiger launched The Tommy Hilfiger Corporate Foundation. With an emphasis on health, educational and cultural programs, the organization supports charities that focus on at-risk American youth. In 1998 Hilfiger was one of several sponsors along with Moet and Chandon, Christie’s Auction House, and The Advocate of the charity LIFEbeat – The Music Industry Fights AIDS. He is also personally involved in charities and causes such as Autism Speaks and the MLK, Jr. National Memorial Project Foundation, and he has served on the board of directors for The Fresh Air Fund, a New York-based group that helps underprivileged children attend summer camp. The Fresh Air Fund’s Camp Pioneer program was renamed Camp Tommy in 1999, in honor of Hilfiger’s patronage.

A professed lifelong fan of rock and roll, Hilfiger’s collections are often influenced by the fashion of music subcultures. The clothes are also marketed in connection with the music industry, and as early as 1993 Hilfiger was an official sponsor for Pete Townshend’s Psychoderelict tour. Hilfiger has also sponsored several musical events, including Sheryl Crow’s If It Makes You Happy tour in 1997, Britney Spears 1999 …Baby One More Time Tour as main sponsor, and Lenny Kravitz’s 1999 Freedom tour. By the mid-1990s, Hilfiger’s style of clothing was popular with both the American “preppy” scene and as hip hop fashion. American R&B icon Aaliyah became the much-publicized spokesperson for Tommy Hilfiger Corporation in 1997.

Hilfiger had a cameo in the fashion spoof Zoolander in 2001, and from 2002 to 2006 Tommy Hilfiger INc. owned the naming rights to the Tommy Hilfiger at Jones Beach Theatre venue. Largely due to declining sales in the early 2000s, Hilfiger began reworking the brand, striving to retain the designer brand exclusivity of the Hilfiger label by signing a deal to distribute the best-selling Hilfiger lines at Macy’s only. The Tommy Hilfiger Corporation continued to work closely with musicians into the 2000s, focusing on fragrances as well as clothes. Sweetface Fashion, which owns the J.Lo by Jennifer Lopez line, was bought out by Tommy Hilfiger in 2003. True Star, a fragrance endorsed by Hilfiger and released in 2004, featured Beyoncé as its poster girl. The Tommy Hilfiger Corporation company had revenues of approximately $1.8 billion, and 5,400 employees by 2004.

In 2005, a CBS reality show called The Cut tracked the progress of sixteen contestants as they competed for a design job with Tommy Hilfiger and their own fashion line under Hilfiger’s label. The show progressed in a similar fashion to Donald Trump’s The Apprentice. After a final competition that involved setting up the display window for Macy’s Herald Square location in New York, Hilfiger chose Chris Cortez as the “next great American designer.”

In December 2005, Tommy Hilfiger sold the clothing brand for $1.6 billion, or $16.80 a share, to Apax Partners, a private investment company. The transaction was completed in May 2006. In 2008 Hilfiger, Rives, and Bar Refaeli co-hosted the Bravo special program Tommy Hilfiger Presents Ironic Iconic America. Based on the book Ironic Iconic America written by Hilfiger and designer George Lois, the program examined how pop culture has influenced American tastes and styles. In 2009 Hilfiger was a guest judge on an episode of Project Runway, and he presented the Best African Artist award to Akon at the 2010 World Music Awards.

Since 2008, Hilfiger has designed limited-edition handbags in support Breast Health International (BHI), an international organization focused on finding a cure for breast cancer. A portion of the handbag sales proceeds is donated to BHI’s Fund For Living program, with celebrity ambassadors appointed for each seasonal campaign. In 2013, Claudia Schiffer and Naomi Campbell modeled the BHI bag in a photoshoot with photographer Patrick Demarchelier.

On December 12, 2008, Hilfiger married his second wife, Dee Ocleppo; the couple had a son in 2009.

Millennium Promise, a non-profit organization focused on eradicating extreme poverty, hunger and preventable disease in impoverished regions, classifies Hilfiger as a Millennium Promise MDG Global Leader, and in 2009 Hilfiger made a five-year $2 million commitment to Millennium Promise. The donation went towards relief efforts in a Ugandan city, with the aim of improving residents’ access to necessities like clean water, education, and farming techniques. In 2012, all philanthropic activities of The Tommy Hilfiger Corporate Foundation were renamed Tommy Cares, a wider-reaching global initiative that further integrates the brand’s non-profit partnerships, charitable contributions, and employee involvement. On a global scale, Tommy Cares continues to support organizations such as Save the Children, the World Wildlife Fund, War Child, and Millennium Promise. Hilfiger and his wife are on the board of Autism Speaks as of 2012, and through the organization, Hilfiger became a sponsor of the Golden Door Film Festival in September 2014.

In March 2010, Phillips-Van Heusen, owner of Calvin Klein and Izod, bought the Tommy Hilfiger brand from Apax Partners for $3 billion. The Tommy Hilfiger online and in-store ad campaign called “Meet The Hilfigers” began in August 2010 and ran through August 2011. In 2011, Hilfiger and a partner signed a contract to buy the Metropolitan Life Insurance Company Tower building for $170 million, planning to transform it into Hilfiger’s first hotel, with luxury condos. Hilfiger backed off the project in September 2011. A guest judge on the finale of Project Runway: All Stars along with Ken Downing in 2012, shortly afterwards he served as a fashion consultant to contestants on season 11 of American Idol.

Hilfiger was instrumental in the creation of the Marc Anthony Collection in 2012, as Marc Anthony had never been interested in the fashion business until Hilfiger called him and convinced him a line was worthwhile. In 2012, Hilfiger was awarded the Geoffrey Beene Lifetime Achievement Award from the Council of Fashion Designers of America. Global sales in retail for the brand in 2013 were US $6.4 billion, and $6.7 billion in 2014. Hilfiger remains the company’s principal designer, leading the design teams and overseeing the entire creative process. In 2016, he collaborated with model Gigi Hadid on clothing designs launching the TommyXGigi clothing collection. On February 8, 2017, the brand will hold its ready-to-wear show in Los Angeles, in the first time the brand will not be part of New York Fashion Week.

In January 2015, Hilfiger announced that he was working on his memoirs. The book was written chronologically over a year, with Hilfiger explaining “I was hesitant to write it, but thought I better do it now because someday I may forget.” Co-writer Peter Knobler had full access to interview friends and family, with Hilfiger citing the candor of Diane von Furstenberg’s memoirs as an inspiration. Calling the writing process “great therapy” and “interesting,” Hilfiger asserted that he “wanted to give people a sneak peek of what goes on behind the curtain [of] how the fashion industry works.” He read selections from the book in June 2016 at the Literacy Partners Evening of Readers and Gala Dinner Dance. Hilfiger’s memoir, American Dreamer: My Life in Fashion & Business, co-written with Peter Knobler, was published November 1, 2016. In a statement, Hilfiger described it as “a roadmap of the moments that have defined both my [40-year fashion career] and my personal life,” and the book covers his childhood, his early business ventures, and his later life in fashion. With Kirkus Reviews calling it “an honest, straightforward, mostly entertaining autobiography,” Hilfiger made an appearance for the book at the Miami Book Fair shortly after its release. American Dreamer appeared on the New York Times Best Sellers List in December 2016

In 2016, Hilfiger also echoed his support for dressing Melania Trump, telling WWD that “any designer should be proud to dress her.”