FASHION ICON DEE OCLEPPO SHARES HOW SHE MANAGES THE ART OF BALANCE AND SUCCESS WHILE SETTLING INTO HER NEW PALM BEACH DIGS.
Photographed by Diego Armando Mendoza
It’s early in the morning, before the blazing South Florida sun has fully risen, and we’re chatting with Dee Ocleppo Hilfiger in her home closet as she glams for our day of shooting—in what can only be described as a little girl’s fantasy. The sprawling room features her glamorous wardrobe and accessories, beautifully on display and meticulously organized for ease with an adjacent vanity room. Next door, and predictably never too far from his beloved wife, is Dee’s husband and fashion legend, Tommy Hilfiger, as he prepares to jet off to a charity function in his hometown. But he had to stick around to get a glimpse of Dee’s first look—of which he enthusiastically gives his praise.
Dolce & Gabbana dress and sunglasses, dolcegabbana.com; Dee Ocleppo scarf and high heels, deeocleppo.com. Photographed by Diego Armando Mendoza CREATIVE DIRECTION BY @SKMCREATIVE.CO STYLED BY CHARLIE RINCON-RODRIGUEZ HAIR AND MAKEUP BY CAROLINA DALI
The deep love and respect between them is palpable—it’s clear they’re not only husband and wife but best friends and partners in all things in life. Together, they share their son, Sebastian, along with their blended family that brings together the Hilfiger clan.
Dolce & Gabbana dress and heels, dolcegabbana.com; Chopard earrings, chopard.com; Graffring, graff.com. Photographed by Diego Armando Mendoza
The question on everyone’s mind who meets Dee is: How does she do it all? From launching her namesake fashion brand, Dee Ocleppo, back in 2012 to taking up the mantle as Judith Leiber’s creative director in 2017, Dee has kept busy professionally. Yet through it all, she’s stayed grounded in her roots as a wife, mom and friend. And in her new Palm Beach retreat, Dee has crafted a home filled with a colorful coastal style that provides the perfect oasis for family time. We were lucky to get a first look at the spectacular abode, and in touring her home, Dee gives us an inside look at how she puts her personal stamp on each living space. Through each room, Dee’s and Tommy’s designer eyes elevate every corner.
Photographed by Diego Armando Mendoza
She proves that, sometimes, having it all is about curating what matters most. Her enduring success comes from nurturing each endeavor with care and vision. In Dee’s world, work, life and leisure beautifully coexist thanks to her balance. We’re thrilled to share Dee’s wisdom and welcome you into her vibrant world.
When did your love of fashion begin?
It started at such an early age. I can remember being so young, and there was a show called The Mod Squad in the ’70s that I used to watch. I was always intrigued by what these characters were wearing. My mom had all these fashion magazines, and I was always looking through them, cutting things out and hanging them on my bedroom doors and walls. And then, of course, I became a model and was surrounded by the industry for many years.
Valentino shirt and skirt, valentino.com; Graff earrings and necklace, graff.com; Davidor bracelet, davidor.com. Photographed by Diego Armando Mendoza
What inspired you to launch the Dee Ocleppo brand?
It started almost as a dare. I was helping Tommy, who was working on the Preppy Collection, and I was telling him about this bag that I used to have, called a Pappagallo bag, and you could unbutton it. I told him he should do the adult version for this collection. And as I was describing it, he said, ‘That sounds cool. You should do it.’ And I thought, why not? It’s a great idea, let’s do it. So, we went to Italy and made some prototypes. And then I took it to Mindy Grossman, who at the time was head of HSN—Home Shopping Network—and she loved the idea. I never really planned to get into it, but it was more something I fell into. Since then, there have been many iterations of the brand as we were pivoting and experimenting to find the best place to land. And now, we’re at a great place and have expanded to categories such as shoes, accessories and handbags.
Valentino shirt and skirt, valentino.com; Graff earrings and necklace, graff.com; Davidor bracelet, davidor.com. Photographed by Diego Armando Mendoza
What drew you to a brand like Judith Leiber to become the creative director?
I’ve known about Judith Leiber for a very long time. It’s one of the few American heritage brands that has existed since the ’60s. Judith Leiber started out by correcting a faulty bag that was damaged, so she went and got crystals to glue on to cover the spots, and that’s how she got started. I’ve loved the brand for many years, so when she asked me to come on board, I was super excited about it because I felt like I could bring something to the table to reintroduce the brand to a younger audience. It was time to refresh, and that’s what we did. We’re also expanding to belts and jewelry now—we have everything from furniture, wallpaper and greeting cards—so it’s really exciting that there are so many opportunities for us.
Roberto Cavalli dress, robertocavalli.com; Ferrari pumps, store.ferrari.com; Davidor jewelry, davidor.com. Photographed by Diego Armando Mendoza
What have been some of the most significant challenges you’ve faced with the two brands? And rewards?
For challenges, it’s definitely much more complicated than I expected it to be. There are so many unpredictable hiccups that arrive, as there are so many different steps from creation to execution. For rewards, it’s been amazing to see how many people have genuinely supported me and helped me grow.
Photographed by Diego Armando Mendoza
Tell us a bit about your new home in Palm Beach. What drew you to South Florida, and this property in particular?
We purchased this house in June 2020. We were in our Miami home at the time and drove up here and were immediately drawn to the place. We thought it was like Miami, just slightly quieter. In the pandemic, Tommy realized he could work remotely, and so many of our friends split time between here and New York; we realized we could do the same. The weather is obviously a huge draw, as is its proximity to New York, where Tommy’s offices are.
Montce swimsuit, montce.com; Gucci sheer shirt, gucci.com; Graff earrings and rings, graff.com; Dee Ocleppo heels, deeocleppo.com; her own headband. Photographed by Diego Armando Mendoza
What has the redesign process been like?
It is a unique, historic home, so we did not do a significant structural renovation but more on the interior design. We try to give a theme or personality to each home of ours. Our Miami home we called our weekend home, so we wanted it to be funky and fun. The inspiration was Austin Powers—it was groovy with lots of pop art; we had scratch and sniff wallpaper and shag rugs. But this is now our home-home, where we reside full time. So we went a little less daring and more conservative. We still had fun—I think it’s quintessential Palm Beach, but at the same time, we brought a fresh and modern vibe to it.
Montce swimsuit, montce.com; Gucci sheer shirt, gucci.com; Graff earrings and rings, graff.com; Dee Ocleppo heels, deeocleppo.com; her own headband. Photographed by Diego Armando Mendoza
You’ve managed to do it all: motherhood, a career and a fantastic marriage. What’s your secret?
I wish I could say that there is a secret, that there’s one magic thing you do, and it all happens. I think it’s just a question of doing your best—sometimes that means pushing yourself, and sometimes that means taking a break and prioritizing what is really important. I also feel the more organized I am, the better I am at balancing it all—so maybe that’s the secret.
Oscar de la Renta dress, earrings and ring, oscardelarenta.com; Chopard necklace, chopard.com. Photographed by Diego Armando Mendoza
You’ve inspired so many women in the fashion world—who inspires you?
It is difficult to pick one person! I am inspired by strong, independent women—women who are working hard to support themselves and their families. I am particularly inspired by single moms who do it all on their own. Many of my friends inspire me—the first who comes to mind is my dear friend Kris Jenner, who manages a large family with their relationships and careers—I look to her for advice a lot. I’m also inspired by women who spend their time selflessly helping others and are incredibly philanthropic.
What impact do you want to leave on the fashion world?
I hope to inspire women in a positive way, especially those who feel they are at an older stage in life and are afraid to start something of their own.
Photographed by Diego Armando Mendoza
Guilty pleasure
REALITY TV
Show you’re binge-watching
ANYTHING REVOLVING “LOVE” ON REALITY TV, LIKE LOVE IS BLIND, BACHELOR IN PARADISE AND THE ULTIMATUM.
Something people may not know about you
I’M HALF TURKISH AND HALF ENGLISH, AND I SPEAK FRENCH AND ITALIAN.
Greatest piece of advice
BE KIND.
Three things you can’t live without
TOOTHPASTE, DEODORANT AND A HOT SHOWER—ALL THINGS NECESSARY FOR HYGIENE!
Favorite
VACATION DESTINATION THE MALDIVES
Bucket list destinations
THAILAND, CAMBODIA AND SAUDI ARABIA
Photography by: Photo By: Diego Armando Mendoza
