By Sydney Sadick
Dee, you’re a CEO, creative director, wife, and mother. When did you feel like the spotlight was on you for the first time?
I definitely felt it for the first time when I started dating Tommy [Hilfiger] in 2006. I had just moved to New York from Monaco, and I think many people wondered, as I was not in the New York social scene, who is this girl and where did she come from.
You co-own and are creative director of the Judith Leiber brand. How do you protect its legacy while still putting your own stamp on it?
Judith Leiber has always maintained a specific heritage and legacy with luxury, quality, and craftsmanship being at its core. As long as we maintain that, we can push the designs in a more modern direction. It’s been a dream come true to create more fun, whimsical, and bolder designs along with my team, and the results have been rewarding.
Your new show, The CEO Club, on Prime reframes success through the lens of female leadership. What do you want people to learn about you from watching the show?
People will definitely learn a lot about me on the show, however, what I want people to learn or take away from it is the only real failure in business is quitting! Failures are lessons, and it’s how you handle them that determines your path. The show is not about me.
Were you hesitant to get into reality TV?
I was incredibly hesitant to get into reality TV…and still am!
Who gave you the best piece of advice leading up to it, and what was it?
Kris Jenner, who told me, “Buckle your seat belt…and have a martini!”
Who are you closest to from the cast now?
I’m the closest with Thalía. We were next-door neighbors in Greenwich, Connecticut, and have known each other the longest and vacationed together many times.
You’ve cultivated an extraordinary circle of women. What do you look for in a friendship at this stage of your life?
Trust and loyalty—full stop and period!
What’s one decision you made that felt terrifying at the time but defined the woman you are now?
I would have to say my divorce from my first husband was the most terrifying decision I had to make at the time, and it definitely changed and defined the woman I am now.
You and Tommy have built something rare—a marriage that thrives inside a global brand. What’s the secret to keeping the romance alive when business is always in the room?
Tommy and I have an amazing relationship built on true love and immense respect for each other. It’s the second marriage for both of us, so I think we approached it with more insight than we may not have had the first time around. We’re both fairly good communicators and try to address issues head-on instead of letting them fester.
You went to the Met Gala a year into dating Tommy. Did you realize how serious your relationship was with that gesture?
The first year I went to the Met Ball was 20 years ago. I was living in Europe, and I had never heard of it and had no idea what I was attending! I wore a simple dress and did my own hair and makeup; I never made that mistake again! In fairness, it also was not quite as extra as it has grown to be today.
Tell us about the process of creating your own Tommy look for each Met Gala, and what people would be surprised to learn!
Each year I get together with the Tommy team and design the look for the Met Gala. It’s very collaborative and usually takes three months from start to finish.
Palm Beach has its own rhythm—a little slower but deeply strategic socially. How has living here shifted the way you build relationships and do business?
I love living in Palm Beach! What I love about my friendships here is that they’re purely organic and not transactional at all. All my friends are in different industries, which is so refreshing. I think living in Palm Beach and doing a lot more meetings by Zoom has made the quality of my life exponentially better.
If someone wanted to live “their best life” the Dee way in Palm Beach, what three things should they prioritize?
Exercising outdoors, eating at some of our great restaurants, and shopping on Worth Avenue.
Is there anything you miss about living in New York City?
I absolutely miss NYC! First of all, I miss seeing my friends there. I miss the energy, excitement, and all the opportunities that living in New York provides. I miss the museums, restaurants, and the people-watching.
You’ve built brands, stewarded heritage, and lived very publicly. What are you building now that no one sees coming?
I’m continuing to work on growing my brands and hopefully will continue with some exciting collaborations. I don’t know what the future holds, but I have to trust and have faith that it will be great.
What’s something people would be surprised to learn about you?
I think many things: I love a good challenge. I have run the New York Marathon and have gone skydiving. I used to work on Wall Street as a commodities broker assistant, and I can speak fairly good French and Italian.
If this chapter of your life had a title, what would it be?
“Seasoned Survivor Still Standing.”
