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Dee Ocleppo Hilfiger Gets Real

Dee Ocleppo Hilfiger

Model. New Englander. Mother. Entrepreneur. Refreshingly honest. Like most women, Dee Ocleppo Hilfiger is many things, including surprisingly down-to-earth. In a recent visit to the Boston Saks Fifth Avenue to promote her eponymous handbag line, the designer, model and wife of iconic American designer Tommy Hilfiger opened up about balance, versatility, and the things she's learned since becoming an entrepreneur. 

Boston Saks Fifth Avenue, Dee Ocleppo

You grew up in New England. How is your background reflected in your handbag line? I grew up in Rhode Island and went to college in Texas. I'll never forget walking into class the first day in my L.L.Bean topsiders, my Levi's cords and an oxford button-down shirt. I looked around and saw the most gorgeous girls with their hair and nails done, makeup to perfection, and they were definitely not wearing L.L.Bean. I thought, "I will never get a boyfriend in college if I don't up my game a little bit." But there is definitely somewhere in-between  - maybe Bostonians can't wear stiletto sandals on cobblestone streets, but you can wear some kind of heel - it's all about balance! 

My line was originally based on this little bag I had in seventh grade. It had little buttons on it, and you could switch out the preppy covers. And that was my inspiration - I remember thinking, "I would love to have a grown-up version of that bag." I've taken that concept and developed it so it's a little less "preppy", although I do think some of the bags translate well to Martha's Vineyard! 

How do you describe your personal style? Classic / edgy. (Ed note: This is pretty much how I describe Boston style.) I love conservative, classic silhouettes. I did design many bags in neutrals like black or beige, but, our winters are so brutal (last winter I remember just wearing constant black and gray), and I just couldn't wait until we could bring out the color. I really embrace color. 

How do you find the balance between a bag that's functional, but also attractive? Something beautiful that is not practical will be very difficult to sell! I really start from the practical standpoint;  the interchangeable covers are representative of my New England practicality. The linings of my bags are all pink, because when you have a dark lining your bag turns into a big, black hole - you can't find anything! I've designed some bags to carry iPhones since I am forever losing mine. I've designed a bag with a wrist chain for cocktails so you can hold your bag while you're shaking hands, holding a drink, and trying to put a canape in your mouth. I'm not interested in something if it is not comfortable or practical. I love being able to actually meet my customers - it's important and interesting to learn from the users of my products. 

Clearly, you have a background in fashion, but starting your own business is never easy. What did you find surprising about starting your own line? I didn't realize that it was so intense, in the sense that you are always thinking a year ahead of the seasons. You're always having to put out a constant flow of product and ideas. Another aspect of the business I had to learn was inventory management, and dealing with our manufacturers in Italy - you don't want to be sitting on product. (Ed note: The inventory struggle isn't just for fashion entrepreneurs!) The accessory market is already over-saturated, so you really have to offer something different. The good news is that the fashion industry keeps producing. Everybody always wants something new - we all love retail therapy! 

Take me back to when you decided to start your handbag line. What was your first step? It's a hard step from idea to reality. Having an idea is easy; executing the idea is difficult. To be completely honest, I would not have even started this business if I wasn't married to Tommy [Hilfiger]. He was doing a preppy pop-up shop and I suggested the idea of the bag with the interchangeable covers. He said "No, I shouldn't do that. You should do it; it's a whole business!" Mentorship is really key - finding someone that believes in you. [Tommy] came up with ten reasons why I should launch the line, and I came up with, like, thirty reasons why I shouldn't. Of course, it would be easier to just stay home; I'm very lucky in that I am not dependent on this business to put food on my table. But it was really about rising to a challenge and being able to be creative and offer something unique. 

I would encourage entrepreneurs to always move ahead. We presented the idea to many people who didn't get it, didn't like it. One of the things my husband taught me is that, in business, when you come across a stumbling block, you figure out a way to go over it, or around it, or below it, you don't just let it stop you. 

What is the biggest challenge female entrepreneurs face, and how do you advise them to address it? It's always about balance. I am one of the lucky ones in that I am able to have help. I have a five-year-old at home; I would not even be able to sit here with you if I didn't have a terrific nanny. That said, while it is true that I have an excellent support system, it's still a struggle; I want to be there for my children! You have to carve out sacred time for your family. I am always there for breakfast with my family and I always take my son to school. I won't take any appointments during that time - it's special. Women have so many things that they have to be and do; to start your own business you have to accept help. Whether it's from your family or a nanny or a friend, you have to accept that you physically cannot do everything and you need to accept help. 

A lot of women might put off starting a business until they get their kids to a certain phase. There is a time for everything; so women should not get discouraged if that is their decision! I'm receiving a "mothering" award soon, and, while I am honored and grateful, I'm almost embarrassed to get that award. I have a lot of help. Mothers have to be cooks, nannies, taxi drivers, psychologists, doctors, teachers, everything. It's nothing short of being a superhero. You just do the best you can; you don't beat yourself up!

If you could say one sentence to your customers, what would it be? Have fun with fashion. 

Interested in starting your own business? Read more from two local, female entrepreneurs here. To see more on TBF from Boston Saks Fifth Avenue, read here and here

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  1. that little one is seriously so cute!

    1. Right? I love mini bags (even though I usually need to carry a gigantic tote).

  2. I love the shape - and yes, that little one is adorable!

    jess | Bows & Bouquets