An Unstoppable Woman: Dee Ocleppo Hilfiger 

Dee Ocleppo Hilfiger 

Written by: Michelle Emmick

Designer, entrepreneur, wife, mother, and philanthropist Dee Ocleppo Hilfiger is an unstoppable woman. Dee was born in Ohio and grew up in Rhode Island near the prestigious Rhode Island School of Design (RISD). There, Dee’s unbelievable journey began, as she found herself enthralled in the modeling world.

“My very first foray into modeling was when one of the students came up to me and my girlfriend on the street and asked us to model in their fashion show,” Dee shared. “That was the first time I ever thought about it or thought I could do it. We modeled in their fashion show, and that’s when I got the bug. I always loved fashion, but that’s kind of what hooked me into it.”

At just 16 years old, Dee began a part-time career in modeling and continued this passion throughout her college years in Dallas. After college, Dee’s passion took her to Paris, where she pursued modeling full-time. 

There’s no question that Dee’s successful modeling career would have lasted much longer, but her behind-the-scenes collaboration with her husband of 15 years, iconic American fashion designer Tommy Hilfiger, ushered in a natural progression toward a path to design. “I never had plans to go into design, yet I always loved it and believe it’s a great creative outlet. I was kind of always on the sidelines whispering in Tommy’s ear, giving my two cents into the collections. One year, he was doing a preppy collection, and I said, ‘You should do a Pappagallo bag like the ones made popular in the 60s. You could change the covers.’ I started describing in depth about this bag. I think he was either bored with all my descriptions or just wanted to distract me,” joked Ocleppo, “but he really encouraged me, and he’s like, ‘Well, why don’t you do it?’”

Dee took her ideas and made a prototype, sharing it with Mindy Grossman, who at the time was head of Home Shopping Network. “I thought it would be a great product to sell and demonstrate on air, and the designs did really well,” Dee shared. Because the handbags were so well received, Dee was motivated to create a highly specialized luxury product crafted in Italy. Dee eventually became the Creative Director of Judith Leiber and the Founder of the Dee Ocleppo Collection and her timeless pieces and designs are sold internationally by high-end retail partners like Harrods and Saks.

After years of traveling the world and immersing herself in style throughout the fashion business, Dee expanded her collection to include exquisite shoes and sumptuous silk and cashmere goods. Dee says she’s inspired by the people and places that have been a part of her experiences. “I design based on the desire of what I like to wear. I would say my style is more kind of classic. I always like to say it’s on trend, but it’s not trendy. I like really good quality things that I can hold onto and keep for a while. I’m not so much into producing fast fashion or things that just are in one season,” she explained. 

According to Dee, there are a few essential pieces that are always great to have in your closet: a versatile blazer, a quality trench coat, a good cashmere sweater, a classic black cocktail dress, and a great pair of slingback shoes. “I just came out with the new spring collection. I have these incredible strappy sandals. It’s not a super high heel; the leather is padded. I’ve never worn a more comfortable shoe,” Dee revealed.

Dee utilizes her fashion expertise in many ways, particularly philanthropy. One of the organizations she’s involved with is GLAM4GOOD, a non-profit organization that celebrates social impact and empowerment through beauty and style. Started by Dee’s girlfriend Mary Alice Stephenson, a renowned fashion and beauty expert, GLAM4GOOD provides life-changing makeovers and transformative fashion experiences for everyday heroes and people in need. “It’s so beautiful to see how fashion and beauty can really uplift people and change their mood and the way they feel about themselves,” said Dee.

As we concluded our conversation, I spoke with Dee about our issue theme, “Better With Age,” and about her personal definition of beauty. 

Dee believes confidence is the key to getting better with age. “I think you’re just more comfortable in your skin, and for me, I’m more comfortable with who I am and more confident. When it comes to fashion, at a certain point, you establish your own style.” 

In the case of beauty, Dee has come to understand that health and self-care are at the core. “I think it has to start with health. Real beauty is a healthy body, healthy skin, and really taking care of yourself. It starts from there, and then it works its way outside.” 

Dee’s passion for fashion and long-standing career from model to mogul is celebrated throughout her brand. You can learn more about her gorgeous collection by visiting   https://deeocleppo.com/. 

IG: @deeocleppo / @mrshilfiger