Even from Elmira’s highest hilltops you can’t see the mega-yachts anchored off the French Riviera, with their swimming pools and helipads and beautiful, suntanned millionaires. No, it’s a world away.

You can’t glimpse the sunlit mansions of Palm Beach, either—or Mick Jagger’s Caribbean villa, or the ski slopes of Aspen.

But if you’re a working-class boy, small for your age, flunking school, with an unpredictably angry father and embarrassed to be seen in his rusted ’51 Pontiac, you can always dream about such places.

And if you’re the ambitious, talented Tommy Hilfiger, you’re going to make those dreams come true.

“I was always planning my escape,” the legendary fashion designer, now seventy-one, would recall years later. Elmira was a mighty manufacturing city, but it felt “provincial” in his youth, the antithesis of all that was stylish and glamorous and what he aspired to be.

Alas, “there was nothing I was good at,” he supposed as a teen, unaware he was severely dyslexic. He felt trapped.

Five decades later his name is an iconic brand sold around the world. Global retail sales of Tommy Hilfiger products reached $9.3 billion in 2021, and his life—well, it’s a classic American success story.

He’s pals with Jagger, his next-door neighbor on the private island of Mustique. Home is a Palm Beach waterfront mansion. In March he sold his ski chalet in Aspen for $50 million. And that 205-foot yacht anchored last month off St. Tropez?

It’s his.

Its name is Flag, after the slender, red-white-and-blue rectangle that’s been the Tommy Hilfiger brand logo since 1985.

Yes, Tommy “escaped” Elmira all right. Yet for all it seemed to a teenager like a “suffocating” small town, the Queen City on the Chemung River served as launchpad to his skyrocket of a career.

“I’m very grateful to have grown up in such a friendly, all-American community,” he says in a phone call from Flag. And he never turned his back on the city.

This month, as part of its growing emphasis on career preparation, Elmira College will formally begin its new Tommy Hilfiger Fashion Business School program. Funded in part with a $100,000 donation from Tommy, the program will introduce aspiring fashionistas to the business side of the fashion industry: marketing and merchandising.

Why? Because it was in 1969 downtown Elmira that eighteen-year-old Tommy and two friends opened what fashion history records as his very first store—and later made some painful mistakes that tumbled their company into bankruptcy. He doesn’t want any young fashion entrepreneur to repeat them.

His cellphone signal from the Riviera is breaking up, but he stays on the line to make this point: “A lot of fashion schools teach fashion design and focus more on the creative. But in reality, the thing they’re missing is the business of fashion. So, I thought it appropriate to set up a program that focuses on the marketing and merchandising of fashion.”

Hometown Connections

In 2019, Tommy’s sister, Betsy, and brother, Andy, pitched the idea of a fashion program to Alison Wolfe, chair of Elmira College’s Business and Economics division and now director of the Tommy Hilfiger Fashion Business School. She “loved it” and quickly brought it to Charles “Chuck” Lindsay, the college’s president.

“I was immediately intrigued,” says Chuck. “It wasn’t just his [Tommy’s] name…I knew he had his roots in Elmira and served on our board. So, this was a way of deepening his connection to the college.”

Founded in 1855 as a first-of-its-kind school for women, Elmira College went co-ed in 1969. Like many small, liberal arts colleges once heavy into English, history, and philosophy, it now focuses on career preparation in specialized fields like actuarial science, sustainability, and health care. And now comes their Tommy Hilfiger Fashion Business School program. It offers minors or concentrations in fashion marketing or merchandising as part of a bachelor’s degree in business administration.

“When we met with Tommy,” Alison recalls, “he told us: ‘I want this to be a three-year baccalaureate so they can jump quickly into the industry or go on to grad school.’” A three-year track “makes us very competitive,” Alison continues, and the “hands-on” curriculum will include guest lectures, internships, semester-abroad opportunities, and field trips to manufacturing companies and the Fashion Institute of Technology (FIT) in Manhattan.

Naming a program for a fashion superstar isn’t just window dressing, says Chuck. “We already have a good reputation for business education, so the pieces seemed to fit together. We saw that this would improve our arsenal.”

Word of the program immediately interested twenty-two-year-old Nicholas Drake, a transfer student. “I was working at the Tommy Hilfiger store in Corning last year,” when Betsy Hilfiger stopped in and shared this breaking news. Self-described as “fashion conscious even as a kid,” Nick, of Horseheads, hopes to “start my own clothing line someday. But I don’t want to jump right off the bat into design. I first want to learn the marketing side of the business—where the numbers come from.”

Suffice it to say, Nick’s approach is a wee more calculated than Tommy’s was.

The now fabled career began one day in October, 1969, when Tommy and his best friend, Larry Stemerman, skipped classes at Elmira Free Academy to tour the cool clothing shops of Ithaca.

“It was the hippest town in New York State,” Larry says in a recent conversation.

Dazzled by the vast selection of bell bottom jeans at a boutique on Aurora Street, the boys implored its manager to open a store in Elmira. “It’s a wasteland,” Larry told him. “There’s nothing to wear!” The guy shook his head. “You guys should open it,” he told them.

They laughed. They were still in high school! But the next day Larry got serious. “Why don’t we open up a store?” he asked Tommy and their friend, Jonathan Allen. The others were dubious, but Larry knew of an empty basement at the Midtown Plaza shopping center, next door to his dad’s shoe store.

“I think it was once a Montgomery Ward store,” Tommy recalls, and “massive” at 5,000 square feet. “It hadn’t been painted or swept in a decade,” and the only access was from a parking lot in the rear of the mall. But rent was $50 a month, and the landlord didn’t even want a security deposit.

Tommy put up the $150 he’d earned pumping gas at a Hess station. The boys enclosed part of the cavernous space with burlap bags, painted the walls black, and called it People’s Place. Tommy even hung jeans from the ceiling. They opened the doors on December 1 and sold all their inventory by the end of the day. The take was $200.

By Christmas, People’s Place was the go-to boutique and head shop for wannabe hipsters across the Twin Tiers, averaging $500 daily.

“And, oh, my God,” Larry recalls with a laugh. “We had all the prettiest young ladies in the world. We didn’t have to think about getting a date. It was incredible. And everybody wanted to work for us.”

A Wonderful Selection for ‘Guys and ‘Chicks, boasted their early newspaper advertising. BELL BOTTOMS. Leather Goods.

Every Body wants to get into OUR PANTS, read another.

A reporter for the Elmira Star-Gazette soon marveled at the rapid success of these “long-haired, mod-dressed youth” who insisted they had neither “joined ‘the establishment,’ nor are they fighting it.” They were hipsters, all right, but entrepreneurs at heart.

“We both had this work ethic,” recalls Larry, now owner and CEO of a prosperous “mid seven-figure” menswear line called TailorByrd. “I did the buying and Tommy did most of the merchandising. He was on one hundred percent of the time: always creative and inventive, asking himself ‘How can we improve our business visually?’”

At times, they even seemed blessed. On June 22, 1972, with Hurricane Agnes pushing into the region, Tommy and Larry drove to the top of Harris Hill for a better look. To their horror they saw the Chemung was cresting its banks and would soon overflow at Elmira. “Tommy!” cried Larry. “This is going to wipe out the whole town.” They rushed back to warn shopkeepers, but even Larry’s father shrugged. The boys and friends and family spent the night frantically loading their inventory into the mall’s only elevator and dumped everything onto the fourth-floor offices of an architect.

People’s Place was saved, but “by seven in the morning,” says Tommy, “the whole town was under water.”

Our hipster entrepreneurs were soon paying cash for Porsches and Mercedes-Benzes, doing drugs, hanging out at Manhattan’s ultra-exclusive Studio 54—even flying to rock concerts in chartered planes.

Then it all collapsed.

“It was a matter of being inexperienced and not really understanding the importance of keeping control of the business,” Tommy explains. Part of the problem was that “we opened too many stores.” And when the bellbottoms, sandals, and beads look of the early seventies became passé, they bought heavily into the “glam rock” look then hot in New York City: silver motorcycle pants, platform boots, and frilly blouses. “All glitter and shine,” he called it in his 2016 autobiography, American Dreamer.

Alas, “glam” was just too glitzy for the young people of upstate New York. People’s Place’s inventory mounted but didn’t move, and in 1976 the guys were forced to declare Chapter 11 bankruptcy. “It was a shocker, because it was something I didn’t expect,” says Tommy. Still, it allowed the guys to restructure their debt, eventually close or sell off the stores, and move on.

Today they’re still friends. “We email, talk on the phone,” says Larry, whose home is in Connecticut. And has he ever been on Tommy’s yacht? “Nah,” he says. “I don’t go in for that stuff.”

“I was itching to see the world,” Tommy recalls now. “I wanted to conquer something, but I knew I could never conquer it in Elmira. I wanted to become a global brand and compete with the best of the best.”

By then he’d developed an eagle’s eye for fabric, stitching, color, and style. He’d met with a lot of designers and manufacturers, too, “and I knew I could do it better.”

Snoop Tommy Dog

Tommy and his girlfriend, Susie Cirona—she worked at the Ithaca store, where they met—moved to Manhattan in 1979. They married, had four kids, divorced in 2000, and he later remarried (Dee Ocleppo).

The full history of his five-decade career won’t fit in these pages, but the short version goes something like this: after designing for several international clothing firms, he launched the Tommy Hilfiger company in 1985. The look was crisp and posh—what he calls “preppy with a twist”—and featured fine details like contrasting stitching and corduroy or chambray (pale denim) collar and shirt cuff linings. The look was a hit, sales took off, and fashion icons Ralph Lauren and Calvin Klein were soon gnashing their teeth over this upstart rival.

In 1992 the Tommy Hilfiger Corporation went public and enjoyed double-digit growth through the decade, fueled in part by a tidal wave of popularity after rapper Snoop Dogg wore an oversized rugby shirt reading TOMMY on Saturday Night Live. The shirt sold out worldwide in a day, the brand grew red hot, the company’s stock split twice, and in 1995 New York Magazine reported he was earning $6 million a year.

But the new millennium proved rockier. The company lost market share, and in 2006 Tommy and his partners sold it to Apax Partners, a private equity investment group, for $1.6 billion. Four years later, apparel giant Philips-Van Heusen bought it from Apax for $3.1 billion.

Today the revived line features numerous collections, including Tommy Jeans, men’s and women’s sportswear, kidswear, licensed lines of footwear, watches, jewelry, fragrances, and Tommy Hilfiger Collection. He wears the title of “founder” and still serves as the line’s principal designer.

“I give my design team the big picture of an idea and they execute it,” he explains. “I was just in Amsterdam where we have hundreds of team members working under me.” He does a lot by Zoom, he says, “so I can work anywhere.”

Even on the fantail of a yacht.

Back to the Future

Some 2,000 Tommy Hilfiger stores now dot the globe. But with none in Elmira, let’s pay a visit to Elmira College’s century-old Hamilton Hall, once the school’s library. Tug at the door and a tall, slender woman greets you with a smile. “Hi,” she says. “I’m Betsy.”

As in Tommy’s younger sister, here to guide me around the college’s Tommy Hilfiger Gallery. It opened in October to serve as an inspiration to students in the fashion business program. Call it a museum. Call it a shrine. Beneath its high, vaulted ceiling—where a portrait of Tommy by Al Baseer Holly gazes down (see it on the cover)—the former reading room brims with memorabilia from you-know-who’s long career.

But Betsy, sixty-eight, wants to acquaint me first with the down-to-earth side of being a Hilfiger, and escorts me to framed family photos in the foyer. Here’s their father, Richard, a watchmaker and jeweler, and their mother, Virginia, “the world’s best mom,” she says, who was a critical care nurse at the local hospital. “People still come up to me and tell me how she comforted them” as a loved one was dying, she says. Devout Roman Catholics, Richard and Virginia raised nine kids in a turreted, clapboard Victorian on W. Clinton Street. Their washing machine had a hand-operated ringer. Thomas Jacob, their second child and first boy, was born March 24, 1951.

Then it’s out into the collection: a kaleidoscopic display of colors and shapes from across the fifty-plus years of Tommy’s career. Here are patterned bell-bottoms from the first years of People’s Place, a pair of faux snakeskin pants, and a gray, fake-fur jacket reminiscent of their disastrous “glam” period. Betsy fingers the fur.

“Ugly,” she says with a laugh.

She then strolls me over to the hand-crank cash register from the Elmira store that replaced the original cigar box. “I’ve had that for more than forty years, stored in my attic,” she says, laughing again. “I took it wherever I went. “

Here, too, are burgundy corduroys lined in paisley, a rugby-striped sports jacket, a denim jacket, and a tailored black leather motorcycle jacket.

“It’s hard to say what decade they’re from,” she muses. “A lot of this stuff was in Mom’s attic.”

Betsy brightens as we get to the mementos of Tommy’s philanthropy, including the gold shovel he used to break ground for creation of the Martin Luther King, Jr. memorial in Washington. (The Tommy Hilfiger Corporate Foundation donated $5 million, second only to General Motors.) Those crystal dumbbells are remembrances of his contributions to the fight against multiple sclerosis, which claimed their oldest sister, Susie, along with plaques recognizing his donations to the fights against autism, Lyme disease, diabetes, and brain cancer, all of which have affected family members. He’s made these causes his philanthropic recipients for many years.

But the collection is far from solemn. Here’s a replica of the TOMMY rugby Snoop Dogg wore on SNL, and photos of Tommy with Mick Jagger and Andy Warhol. Here are boots he designed for singer Lenny Kravitz, denim cutoffs made for Mariah Carey, and T-shirts from the Rolling Stones 1999 No Security tour.

It’s a lot to take in. But for Elmira College student and recent visitor Linda Avery, of Tioga, Pennsylvania, the gallery offers a magical mystery tour of the industry she hopes one day to enter—by way of the Tommy Hilfiger Fashion Business School.

“I always liked clothes as a kid,” explains Linda, twenty-two. “I loved to do dress up and put styles together and draw ideas I had in my head,” and as a teenager she would dress the mannequins at the Goodwill store in Wellsboro.

Now, as a student in the Tommy Hilfiger Fashion Business School program, she dreams of beginning her own business as a fashion advisor to clients or designing her own line.

“But if I only have design under my belt, it’s not going to help me,” she says. “You also need to understand marketing, and what financing you’ll need.”

Asked what advice he would give now to young Tommy as he was starting his career, Tommy pauses a moment. There’s faint static on the cell signal—or is it the Mediterranean crashing on a distant beach?

“I might have sold my People’s Place interest earlier and moved to New York,” he says. “But I don’t regret anything. I’ve been very fortunate, and I enjoy working hard because success is not just about luck, it’s about having a goal. And I’ve reached a lot of my goals.”