Dee Ocleppo Hilfiger Interview
The designer, entrepreneur and creative director of Judith Leiber Couture invites us into her fashionable life.
By Tessa Trudeau
While vacationing with husband Tommy Hilfiger aboard their yacht on Italy's Amalfi Coast, Dee Ocleppo Hilfiger graciously took a call from us to talk about her world of fashion. Ocleppo Hilfiger, a former model, has a knack for dressing the part with grace and good-natured ease, whether she's jet-setting around the globe, doing business in Manhattan or unwinding at her Connecticut home. The creative director and co-owner of the playful luxury handbag brand Judith Leiber—now available at Nordstrom—shares her style tips and favorite pieces, including the one dress she'll never get rid of (she was wearing it when she met a special someone).
How would you describe your personal style?
Easy, comfortable, feminine; I try to keep it vibrant and classy. And, of course, there's a lot of red, white and blue in my wardrobe!
What's one thing every woman should have in her closet?
A black turtleneck.
What's something in your closet you'll never throw out?
I have a Missoni dress from the early 2000s, and it's the dress I was wearing when I met my husband. The elastic has all given out on it, I can't even wear the dress anymore, but I refuse to part with it.
What's the most unexpected thing in your closet?
A long, vintage suede patchwork vest with studs. It's very random. I look at it often and think, "Why did I buy this? What am I going to wear this to?" I'm like, "What was I drinking when I bought that?!"
What's your biggest fashion weakness?
Bags and shoes, definitely. There's no question. I have enough bags and shoes for 10 lifetimes. It's my obsession, my passion—and it's also my work.
Tell us about your personal Judith Leiber collection.
One of my most recent acquisitions is the Stack of Cash bag. They're all so much fun. When I'm not wearing them, they're displayed on a table in my dressing area and I get so much joy just looking at them!
Have you gotten any fashion tips from your husband?
Whenever I wear an ankle boot or a shoe with an ankle strap on it, he tells me that they can make your legs look shorter than they are. I always have that in the back of my mind when I'm buying shoes.
What's one styling tip you learned from your modeling days?
Before I started, I actually thought models walked around in these clothes that they're modeling. But I soon discovered that, most of the time, they're wearing jeans and T-shirts and keeping it quite simple, not wearing tons of makeup. So I learned that less is more, and that was a valuable lesson I've carried through the rest of my life.
What about beauty tips?
A smoky eye is always better with a nude lip. It goes back to the same thing—less is more. You don't want to do a really strong eye and then have bright red lips.
What's your favorite city for fashion?
I find the most interesting city for fashion to be Tokyo. I think they're really daring and kind of crazy; it's inspiring. I love checking out what people are wearing.
What are your summer travel plans?
We've been in Europe for most of the summer, and then I come back in August and I'm leaving for an Alaskan cruise for one week. It's a bucket list thing, so I'm super excited about it.
You spend a lot of time at your home in Connecticut. How does your style change from city life to there?
In Connecticut I'm definitely in more relaxed casual wear, things like sneakers and jeans and more comfortable attire. When I'm in the city, I'm usually in more sophisticated silhouettes; oftentimes I'm in black, and I'm usually in heels.
What are you excited to wear this fall?
I just bought myself a beautiful Dior vest that I'm really looking forward to wearing. And I'm looking forward to wearing Tommy's new collection with Zendaya. It's got a lot of beautiful pieces and there are quite a few polka dot things, which I love. I'm looking forward to pulling out my coats and jackets and cashmere sweaters and wearing colors like burgundy and chestnut again—those kind of beautiful fall colors that you don't normally wear in the summertime.