Dee Ocleppo Hilfiger On Finding Love Again

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In the early 2000s, Dee Ocleppo Hilfiger found herself living in Monte Carlo, newly split from her first husband, and she felt stuck. “I was traumatized from my divorce,” she tells Rachel Zoe in the latest episode of Climbing in Heels. “I was like, ‘I have my kids. I will never get married again.’”

Cut to three years later, and her never-say-never mentality was challenged. While on vacation in Saint Tropez with her kids for the Bastille Day holiday, she serendipitously met Tommy Hilfiger. “He was separated; I was divorced,” she says. “He had a daughter diagnosed with autism, and I had a son with it. That was an immediate I-get-you moment.” That understanding became the foundation of a now 15-plus year marriage: a combining of families that includes seven children, three of whom have been diagnosed with varying degrees of autism. The couple is involved in different organizations, including Autism Speaks and Next for Autism, which deal with milestones that occur later on in life, like finding housing or jobs. “The difficult part I find with autism is not when your children are living in your house and you can control things,” says Ocleppo Hilfiger. “The biggest struggle for me was who is going to protect them when I’m not here.”

Now that her youngest child, Sebastian, is a teenager, Ocleppo Hilfiger has added “working mom” to her list of credentials. “I always wanted some form of my own independence,” she says. “I love to work. It gives me a creative outlet. I get to meet people.” Beyond her own brand of luxury leather goods, Ocleppo Hilfiger also serves as Creative Director of the legacy bag brand Judith Leiber (of which the couple owns 20%).

“It doesn’t matter what field you go into,” she says. “You have to be passionate, and you have to work hard.”

Despite her demanding schedule, Ocleppo Hilfiger is always looking forward, pushing herself toward what’s next. “In the fashion business you’re forced to look ahead,” she says. “I look at Tommy, and he’s got 30 years on me. And I’m like, ‘I’ve got a lot of work to do. I’ve got a lot of climbing to do.’”