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Dee Ocleppo’s versatile bags are garnering positive reviews for their uniqueness and quality.

Photo courtesy of Hudson’s Bay/George Pimentel

Tommy Hilfiger knows a thing or two about brand building. The native of upstate New York wowed the fashion scene when he founded his own corporation back in 1985, after years of hustling in the garment trade, and, as legend has it, even selling jeans out of the back of his car. Tommy went head to head with Calvin Klein and Ralph Lauren and managed to build an international fashion empire, becoming a household name and one of the most famous designers in America today. These days, Hilfiger is doing a little mentoring, coaching his wife of almost seven years, Dee Ocleppo, as she builds her own upscale handbag brand.

Ocleppo, a former model who was once married to Italian tennis pro Gianni Ocleppo, was raised in Rhode Island but lived in Monaco for a few years, raising her two sons. She met Hilfiger in 2006 and two years later, they married. A year later, she gave birth to their son Sebastian, the youngest in their combined clan of 7 children. Designing handbags wasn't a lifelong dream for Ocleppo, but rather something she just took up three years ago. Evidently, she's a quick learner. Her versatile, eye-popping bags, some of which have interchangeable panels and which range in price from a few hundred to a few thousand dollars, are being lauded for their originality and luxe quality. I caught up with Ocleppo at The Room at Hudson's Bay in Toronto recently, where Ocleppo talked to me about her editorial eye, her love of challenges and what her husband has taught her so far.

We're all exposed to so much fashion these days. Does the editing process get easier as you go along? Is it easier to know exactly what you do and don't like or do you start embracing new looks?

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I think it does get easier, because I'm always looking for something a little bit different. When you're exposed to a lot, you can start thinking, "Oh, I have that," or, "Oh, I've seen that," and my eye at least is always looking for something that I don't necessarily recognize… something just a little bit different than what I'm used to seeing. I call my style "classic edgy." Maybe in my twenties I could say I was more edgy, but I'm nearly 50, so now I like more of a classic silhouette with a slight edge.

Bags have become the new shoes. We can't seem to get enough of them, and we love all kinds, and all colours and textures. That's something we're all having a lot of fun with. But how hard is it to maintain your unique voice in such a sea of options?

It's very difficult because you can't really reinvent the wheel, but I think that I have a certain aesthetic. For example, the linings of my bags are all pink because I'm so tired of digging into those black linings, where I can never find anything. It's like a big black hole! Also, the covers are interchangeable on some of the bags. That, I think, is something different that is not already offered. But in retail today, there are more choices for the consumer than ever. You walk through these huge stores and they're just full of stuff. So how do you stand out and how do you set yourself apart and offer something that's not already offered? It's definitely a challenge, but I think that I have risen to the occasion and offered something that is not out there. I also don't manufacture a lot of bags; I like to keep it sort of exclusive and special.

Like most young girls, you grew up loving fashion. But what encouraged you to take the plunge and create your own products? Was it Tommy?

It definitely was 100 per cent Tommy. I mean, I would never dare…. I think we're all designers in our mind, even in the way we pick and choose outfits and accessories to wear. But not all of us go to factories to manufacture and invest the money to actually make their own products. That's a scary thing. But anyone who loves fashion and gets themselves dressed in the morning I consider to be a designer.

What's the best lesson you have learned from Tommy so far?

I've learned a lot of lessons from Tommy. But he has this spirit about him that has no fear. He has this sort of "go for it" attitude. I tend to be more cautious and maybe more cynical and I can think of about 10 reasons why I shouldn't have done a bag line. But Tommy will think of 20 reasons why I should do a bag line. So it's a balance. I find myself constantly teetering on that. I want to be optimistic but I want to be cautious, and he just has more of an almost childlike naiveté. I wish I could have more of that.

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Having known him for three decades, I know what you mean. And he knows how to build a brand like few others on the planet know.

It's because he just dives in and he's not afraid to do anything. He's not afraid to call anybody, he's not afraid to go up to anybody…. I'm a little bit more reserved and shy. But I think we have a good working balance.

This interview has been condensed and edited.

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