This Women’s History Month, we’re putting a well-deserved spotlight on female founders in the fashion, beauty, and lifestyle space. Next up, Dee Ocleppo-Hilfiger. The former model turned designer and philanthropist has seen her namesake accessory brand take off since its inception in 2012 thanks to a focus on classic design (her husband Tommy Hilfiger is the legendary purveyor of wholesome American style, after all!). Never one to rest on her laurels, the mom-of-three is also the creative director of Judith Lieber—whose famous sparkly and quirky designs likely need no introduction. Here’s how she gets it all done.
Tell us your backstory! You were originally a model—did you always know you’d end up in the fashion business?
I was raised in East Greenwich, Rhode Island. Like a lot of young girls, fashion was something that inspired me early on, and I started to model at RISD for a lot of the graduate students showcasing their collections. It was always more of a passion project that I did for fun, until photographer and talent manager Jean Renard (who was known for discovering 90s Cover Girl model Niki Taylor) discovered me and encouraged me to pursue a career in modeling.
What drew you to the fashion industry?
For a lot of young girls, it’s something exciting to think about and it was always something fun for me. There’s a certain allure and glamour around the fashion industry. The longer that I worked, the more that I have become invested in fashion, and the more that I’ve come to understand the industry as both an outlet through which to channel creative energy and ideas, as well as a way of showing personal style and individuality.
What moments led to launching your own brand?
Back in 2009 or 2010, Tommy was working on a preppy collection, and I really grew up in that preppy era. I used to wear oxfords and polo shirts with whales on them. I had this little bag called a “Pappagallo” bag, which is also referred to as a “Bermuda” bag. It had wooden handles and fabric covers. I remember my bag had a green corduroy cover, and I told Tommy that he had to have this bag in his collection. I suggested that he make an oversized version for adult women; to which Tommy responded: ‘Well, you should do it!’ I started making prototypes of this bag with reversible covers and then brought the bag to Mindy Grossman of HSN. I explained that I designed a bag based on something similar that I had carried in high school with changeable covers. Mindy was blown away and so we started selling them on HSN immediately. After seeing this design become an immediate success, I decided to focus on the finer details. I continued to find ways of refining and improving my designs, which led me to begin working with more precious silks and fine Italian leathers, and teams of artisans who were classically trained and apprenticed in generation old hand working techniques.
View this post on Instagram
You have two very busy roles. What does an average day look like for you? How do you manage both?
I think I have many busy roles. I am a wife and a mother before anything else. Family always has, and always will, come first. My family is what keeps me centered and focused. Once everyone else’s day has started, I can then begin to think about my design work for Dee Ocleppo and for Judith Leiber, as well as my philanthropic endeavors for BCRF and some of the other charities I support, before it’s time to think about dinner when our family reconvenes and reconnects after our day.
Is there a message you want to send with both brands? How do you differentiate?
I like to think that what I create under my namesake brand, Dee Ocleppo, is the day-time counterpart to the nighttime glitz created for Judith Leiber. I think of Dee Ocleppo as closet staples and pieces meant to accompany a woman in her every day, whereas the evening glamour crafted for Judith Leiber is something to be carried more on occasion, as well as something that I like to keep on display as an objet d’art that sparks joy.
What and who keeps you inspired?
Above all, family is what keeps me inspired. Part of the fun in my work is that my husband is a designer, and we are always sharing ideas, exploring art, and discovering multi-disciplinary talents together; especially based in one of the cross-cultural capitals where art and fashion come together—here in Miami.
What advice would you give other women who want to become a founder or creative director of a brand?
The most important advice I think I could give to women is to never underestimate yourself or your value! Remind yourself daily of your worth, strength, and vast capabilities.
If you could say something to your younger self, what would you say?
I would tell my younger self to just keep confident and continue to trust in yourself.
In your opinion, what is the most powerful thing about being a woman in business in 2021?
I think the most powerful thing about being a woman in business is that I have my own business, my own voice, and my own earnings to support myself. I also find it incredibly empowering to be a woman who designs for other women.
View this post on Instagram
What is one thing that you are grateful for in your career journey?
The one thing that I am grateful for in my career journey is the encouragement that I was given as a young girl. I don’t know if I would have pursued modeling and moved to Europe to further my career if I hadn’t been given that encouragement. It was that boost in confidence that had I needed to move forward in a way which ultimately led me to the exactly where I am today in my personal and professional life.
What is your vision for the future of both brands?
The work done for Judith Leiber is similar to the design process used to my namesake brand. I like to create things which haven’t been done before. I think about what people want. Most important, I ask myself: What will make people smile?