Tommy Hilfiger and Dee Ocleppo Hilfiger have ruled the fashion industry together for nearly two decades, though it's time for that spotlight to shine brighter.
Dee, 59, will be appearing in a brand new Amazon docuseries, The CEO Club (which premieres tonight, February 23), following "a group of trailblazing female CEOs as they navigate the triumphs and challenges of both their professional and personal lives," per Prime Video.
"I'm blessed to have an incredible relationship with a man that I adore, and that I love and respect," she said in the show's introductory episode. "We have Sebastian. He is on the spectrum. I also have two kids from my first marriage."
For as long as she and Tommy, 74, have been together, they've often kept their family life out of the spotlight, especially as their brands continue to grow. Take a walk with us as we dive deeper into Dee Ocleppo Hilfiger's life, her marriage to Tommy, their blended family, and of course, her own brand…
© Getty ImagesMeet Dee Ocleppo Hilfiger
After graduating from Southern Methodist University with a degree in Communications, Dee's career in the fashion world first began as a model.
She was discovered by photographer and filmmaker Jean Renard and as a model, she worked most extensively in Europe. She started modeling in high school, continuing through college and then a few years after before calling it quits.
© Getty ImagesThe Dee Ocleppo brand
Dee devoted much of her life after quitting modeling to her marriage and raising her kids, before pivoting back into the fashion world in the early 2010s with the launch of her eponymous label, best known for its vintage-style luxury pieces, especially the interchangeable and customizable handbags.
The designer once told Boston Common magazine that she describes her bags as simply "special," adding: "I would say it is edgy-classic, because I like classic silhouettes, but then I like a twist. You can have a beautifully tailored jacket or dress or a beautiful silhouette in a bag but if there's something a little bit special about it, it draws the eye."
In 2017, her brand partnered with Judith Lieber, which made her the brand's co-owner, creative director and global ambassador.
© Getty ImagesHer first marriage
In 1997, Dee married Italian tennis player Gianni Ocleppo. She moved to Monte Carlo, where she lived for 13 years, and they welcomed two children together, Julian and Alex Ocleppo.
Julian (pictured here) has followed in his father's footsteps and is now a tennis player as well, achieving a career-high ATP ranking of 309. Gianni and Dee split in 2003.
© Getty ImagesDee and Tommy's relationship
In 2005, Dee met Tommy while on vacation with her sons in Saint-Tropez. The pair connected over having children on the autism spectrum, with Dee recalling to Haute Living of when they first met: "When I found out it was Tommy Hilfiger, I assumed that I would be going on his boat with he and his boyfriend. I wasn't even aware that he was a straight designer!"
After developing a friendship, love blossomed for the pair. They held a lavish New York City engagement party attended by the likes of Anna Wintour and Russell Simmons, before finally tying the knot in 2008.
© Getty ImagesTheir seven children
In 2009, Tommy and Dee welcomed their only child together, a son named Sebastian Thomas Hilfiger. Aside from Julian and Alex, Tommy also has four other children from his marriage to Susan Cirona (1980-2000), daughters Ally, Elizabeth and Kathleen, and son Richard (pictured here).
Several of their kids are part of the elite social circle in one way or another, with Ally previously appearing in MTV's Rich Girls, and Richard performing as rapper Ricky Hil. Three of the couple's seven children have also been diagnosed with autism, and the Hilfigers are passionate advocates and beneficiaries for Autism Speaks.
