Living The Dream

We spoke to iconic man-turned-global-megabrand TOMMY HILFIGER during his first trip to Australia

- Rachel Sharp

It’s 1969, man’s just landed on the moon, Woodstock’s worked its way into music festival lore, and in the small town of Elmira, upstate New York—former home of American literary figure Mark Twain —a high-school kid with big dreams called Thomas Jacob Hilfiger starts selling bell-bottom jeans out of the back of his van.

Young Tommy studies the business of fashion after school, makes his way to the Big Apple, works for various labels, eventually founds his own, then begins a decades-long professional adventure that sees him become a household name. Just like his contemporaries Calvin Klein and Ralph Lauren, Hilfiger’s name today is synonymous with all-American luxury style; his eponymous company’s signature red, white and blue logo literally signifies the Western rags-to-riches dream come true.

He’s rubbed shoulders with A-list celebrities; underwritten the creative endeavours of rock stars, pop stars, supermodels and even fine artists; pioneered a risky but profitable new way of selling from the fashion week runway coined ‘See Now, Buy Now’; donated a ton of time, energy and money to charities (including Save the Children, World Wildlife Fund and Autism Speaks) and won a Lifetime Achievement Award from the prestigious Council of Fashion Designers of America. All the while raising a blended modern family— Hilfiger and his wife of 11 years, designer Dee Ocleppo, have seven children between them.

“The fashion industry is rarely nine-to-five, so my days vary, but no matter what, I always try to wrap early to spend time with my family,” he tells InStyle. “Once our son, Sebastian [now 10], is in bed, Dee and I like to read, watch a movie or catch-up with the rest of our family by phone.”