We had the good fortune of connecting with Dee Hilfiger and we’ve shared our conversation below.

Hi Dee, is there a quote or affirmation that’s meaningful to you?
“Keep Calm and Carry On” I love this quote as it is relevant in every situation, whether personal or business. It is so important to keep a cool head, and not make decisions out of fear or impulse. 

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I have loved fashion from a very young age. I used to read my mother’s Vogue magazines and decorate my room with torn pages from magazines. My first foray into the industry was when I was 16 and I started to model. I entered a local modeling contest and won . From there I was inrtroduced to agencies in New York and Paris and loved working with designers , photographers, makeup artists and hair stylists. I loved being surrounded by so many creative people. When I stopped working in the mid 90’s to have children, I really missed the people and the creative processes that I had enjoyed while working. When I met my, second husband , Tommy , I was once again propelled back into the industry that I loved and missed. It was my husband Tommy, that encouraged me to start my own brand. I started with an idea to design handbags with changeable covers and eventually sold my unique patent to Kate Spade after 2 years. I have found that nothing has ever been come ” EASY ” but having support from family , friends, and colleagues is a must if you really want to suceed at anything. I have learned it is always a team effort and you will always need the help of others. My biggest challenges have always been to stay inspired and continue to exceed expectations I set for myself. I want to continue to surprise others, but more importantly myself. I am very proud of my work at Judith Leiber and how we have been able to reinvent , and keep the brand relevant, youthful and fresh. We have had had much sucess since my appointment as partner and creative director. I am also extremely proud of my ability with my own brand, Dee Ocleppo, to provide an extremely high quality product, inspired by my own taste and style , in the affordable luxury space.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Tommy and I reside in Greenwich, so we are able to enjoy the best of Greenwich as well as the city. I would definitely start in the Greenwich area and take them to Greenwich Ave for some shopping and lunch at le Penguin. For dinner we would head to Rebecca’s for some Martinis and corn bilinis with caviar. The next day we would journey to the Stanford antiques district and enjoy treasure hunting among the several antique emporiums that are all closely located then head to L’escale to enjoy a waterfront lunch back in Greenwich. For dinner perhaps we would head to Polpo for a fabulous and authentic Italian meal. I would also venture to Bedford and Pound Ridge and a walk at Scotts Corners. for the best Pizza in town we would have to head to Fortina in Armonk. I would then head to the city to take in a Broadway show and dinner at the Polo Bar. I would take them to Hudson Yards for some more shopping and a selection of great restaurants, A walk in Central Park and then a Pasta Alla Vodka at Carbone downtown. I would definitely have to incorporate a spa moment either at Tracy Martyn or SkinProLogica.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Too many people to shoutout to, but I would like to dedicate my shoutout to my parents, my 6th grade teacher MaryAnne Artisani, and my Husband Tommy Hilfiger.

Website: deeocleppo.com judithleiber.com
Instagram: @mrshilfiger @deeocleppo @judithleiber
Facebook: deeocleppo
Youtube: deeocleppo

Image Credits
Tatijan Shoan

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