Dee Ocleppo Hilfiger, designing woman

The new creative director of Judith Leiber talks handbags, balancing work and family and life with Tommy.

There are goddesses, and then there are goddesses — you know, the women who are as lovely in grace as they are of form and face.

Dee Ocleppo Hilfiger is one of those goddesses. We first met Dee when she served as a panelist for the Bruce Museum’s provocative “Art of Design” fundraiser, which we covered in April WAG. We were struck then by how grounded she is for someone who is co-owner, creative director and global ambassador of the Judith Leiber clutch and accessories brand and wife of designer Tommy. 

Spend time on Dee’s website and you’ll see that grounded translates into well-rounded. This is one lady who does everything she puts her hand to well, whether it’s launching a new Judith Leiber collection this holiday season or whipping up the protein pancakes (cottage cheese, rolled oats and eggs) that are a favorite of Sebastian’s, her son with Tommy. The former model is also the mother of two tennis-playing sons from her first marriage to former Italian ace Gianni Ocleppo and stepmother to Tommy’s four children from his first marriage.

Family, including Tommy’s eight siblings, is of paramount importance to Cleveland-born Dee, who grew up in East Greenwich, Rhode Island — the daughter of a Turkish radiologist (father) and British microbiologist (mother).

Today, she divides her time between the Hilfiger home in another Greenwich — Connecticut — and homes in other locales while serving with Tommy on the board of directors of Autism Speaks — an organization founded by Bob Wright and his late wife, Suzanne (WAG November 2014). (The Hilfigers have two children who have been affected by the disorder.) Dee is also on the board of Glam4Good, designed to spur social change through style.

How does she manage it all? With some sleep and a great deal of passion:

Dee, we loved the versatile handbags you created under your own label (now part of Kate Spade) and what you’re doing with Judith Leiber. Why did you decide to create handbags as opposed to another accessory?

“Since a very young age, I have always had an obsession with handbags. I remember digging through all my mother’s handbags as a child looking for candy and loot, and I remember always admiring her collection.”

Does a handbag as a fashion item say something about a woman that no other accessory does?

“I believe a handbag says a lot about a woman’s taste and personality.

Is she edgy or more conservative? Does she need a lot of stuff with her at all times or is she fine with fewer items? Is she a working girl or a stay-at-home mom? Does she care more about design and status or functionality?

What’s new for the collection this fall?

“My latest endeavor is the first holiday collection I have designed as creative director of Judith Leiber. I love this brand and we have done some very fun, edgy and exciting new styles.” 

Your website is about a way of life, particularly with a large extended family. What’s the secret to your work-life balance?

“Work-life balance can be tricky, but the first secret is to love what you do. If you really love what you do, the balance is more seamless and less tiring.

I also think, above all, health and getting enough sleep is crucial when you are juggling a large family and work obligations. Strength and mental focus affect not only your decision-making abilities but your interactions with everyone around you. Make sure not to forget to care for yourself while taking care of the rest of the family.”

You and Tommy have done much to raise awareness of the autism spectrum. Do you think the public now has an understanding of it or are there still misconceptions? Any plans for fall events?

“I believe that there are still many misconceptions and misunderstandings about autism. It is a very broad and complex condition that differs dramatically for every individual, and the most frustrating part of it is that a cause or cure still has not been found.

“I look forward to our upcoming event on Nov. 18 called ‘Night of Too Many Stars,’ where some of the world’s most hilarious comedians perform stand-up and skit routines in order to raise money and awareness for autism. Definitely my favorite fundraising event by far.”

Is there a particular exercise that’s your go-to for de-stressing?

“Going for a walk outside is my favorite way to get some exercise and de-stress.

“I usually go with my husband and it gives us a chance to talk about a lot of things we wouldn’t otherwise get to discuss during our busy days.”

I know you and Tommy are big tennis buffs. Will we see you at the Open and do you have a rooting interest?

“Tommy and I both love tennis and have become quite close with Rafa Nadal. He was our global spokesmodel for both our underwear and tailored clothing campaigns.”

Who’s your favorite designer, apart from Tommy?

“I would have to say I love and wear a lot of Valentino and lately Johanna Ortiz.”

Is there one beauty ritual/product that is always a must?

“I think beauty always starts with good hygiene so, as an example, I absolutely cannot fall asleep without first washing my face and moisturizing.”

How would you sum up your philosophy of home décor and home life?

“I think our philosophy of home décor and home life is avoid clutter, stay organized and surround yourself with people and things that you love.”

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