DEE OCLEPPO HILFIGER has led many lives. She’s been an American model living in Paris. She’s been an American wife (to Italian tennis pro Gianni Ocleppo) living in Monaco, where she raised two sons.

And now, the Rhode Island native is back in the US, married to Tommy Hilfiger, raising another young son, and heading a handbag brand that has already been picked up by Saks Fifth Avenue, Harrods, Hudson Bay and Galeries Lafayette in its first year on the market.

Named Dee Ocleppo, the (mostly) eponymous line is noticeably missing the “Hilfiger” moniker, although Tommy is a partner as well as a mentor, and, for the #GirlBoss, a case study. “I can see what’s going on with my husband's company, so I can really enjoy this period as a new brand,” she says. 

No doubt Hilfiger’s advice has thus far proven valuable, as the line is already ahead of the curve by incorporating e-commerce into its business model early on, while it’s taken many other luxury bag lines years (or decades) to try to stand on shaky "e"-legs.

And Mr. Hilfiger plays no small part in the brand’s successful start outside of the boardroom, as well. He dotes on his wife; during the interview, he came into the room with a tall Starbucks cup for Dee, who was in the midst of a busy East Coast promotional tour that extended up to Canada the night before. “Do you want that stuff shipped? All of it? Ground?” he asked excitedly, then turned to me with a mischievous smile, apologizing for the interruption. “Sorry about that. A little, uh, business,” he said. Later that evening, at a fundraising party in the handbag department at Saks Fifth Avenue in Boston, he energetically rushed between women, opening bags to show them the lining and racking up sales for the brand. (And for a great cause - 10% from each Dee Ocleppo bag sold was donated to the Breast Cancer Research Foundation, the recipient of the night’s fundraising fete.)

Even without Hilfiger, the colorful bags, which seemed to come with their own Caribbean breeze, drew admiration, as much for their architecture as for their dynamic - and interchangeable - prints and textures. Indeed, a driving principle behind Ms. Ocleppo Hilfiger's line is versatility, and most of the bags are customizable, whether it’s a removable chain strap or a reversible python panel that slips over the bag’s front. 

The current collection, which ranges from $495 for theEditor's Envelope Clutch in faux crocodile (python is $995) to $2995 for apython Palm Beach or a largePortofino Tote was inspired by Mustique, where the Hilfigers have a home. The next collection, coming this Fall, was inspired by Turkey, where Ms. Ocleppo Hilfiger's father was born.

UNTOUCHABLES: What’s the hardest part of starting a fashion brand?

DEE OCLEPPO HILFIGER: It’s difficult to break into the market as a new brand. I’m competing with the Guccis and the Louis Vuittons and the Celines of the world, so it’s hard to get a foothold on that ladder. Those brands are so established, and for a lot of women, there’s a trust that goes along with that. It’s a bit difficult no matter what you’re doing to get people to take a look at a new brand.

Brands like Chanel or Celine have their iconic bag or their iconic aesthetic, and sometimes it seems young designers need to constantly generate and come up with outrageous new designs.

The iconic Chanels and the Guccis, they’re iconic because they've been around forever. You can’t really compete with that, but as a new designer you have to somehow make your niche, your rung on the ladder.

On the flip side, what’s the best part of running your business?

The best part is being creative and being able to meet people face to face. And it’s kind of fun to be in the beginning stages because we’re a very small company; [everyone’s] role is whatever it needs to be that day. It could be vacuuming the floor - everybody kind of does what they need to be doing.

We’re small and kind of unstructured compared to something like my husband’s business that has gotten so corporate and so big. Mine is a chaotic - organized chaos - gem.

I always compare it to the opposite end of the spectrum - a big company such as my husband’s - where before a decision is final it has to go through so many people and weeks and weeks and weeks go by, and then sometimes that decision isn’t even pertinent anymore. He calls it “analysis paralysis”. We’re just a small, tight company and we can decide on the spot - yes or no, and it’s done. It’s much more hands-on, and I’m really enjoying this period.

What’s the biggest milestone that you've achieved with your brand so far?

Staying in business. Just being here today. There are so many young brands, whether it’s Band of Outsiders or Reed Krakoff, that have started out and it’s a very cash-intensive business and it’s very difficult to stay afloat and stay in business. You've got a lot of really young, talented people that can’t sustain the business. It’s difficult in retail today - a lot of stores want to bring you in on consignment, and there’s a lot of competition. It’s a tough business, and I've learned that. You don’t want to be sitting on too much inventory because that can shut your business down. There’s just so many things that can put you out of business, and I’m lucky enough to have my partner and my husband who’s been down that road - he’s also been bankrupt when he first started out and I’m benefiting from all the mistakes and pitfalls he’s already gone through and see other designers go through.

Access to an archive of experience like that is really priceless for a new brand.

It’s priceless, so I consider myself being not 10 steps ahead, but more like 100 steps ahead, and that’s why I’m moving cautiously and slowly.