Looking at the writing instruments and office supplies the humble stationer was already producing, Sebregondi tried to envision the center of the set, an object with emotional and symbolic strength. A contemporary classic — a leatherback, lined-page journal with an elastic band closure — was born.

Seventeen years later, spin a rotating rack of Moleskine journals in just about any bookshop or office supply store, and you’ll see organizers and paperback cahiers as well as journals branded with characters from Peanuts, Star Wars, and the Little Prince. Planners alone number 90 different styles now. Some die-hard Moleskine fans are surprised to learn the brand designs and sells a wide range products beyond journals, including pens, bags, wallets, and tablet and laptop covers.

The company also has set up several cross-platform collaborations recently. Just this year alone, Moleskine unveiled new partnerships with software giant Adobe and smartpen purveyor Livescribe, planning to roll out the first Moleskine-Livescribe product line in late November. Moleskine also partners with Evernote, most recently offering a free trial of the cloud-based archiving service to customers who buy an Evernote-branded Moleskine notebook.

“The most fascinating thing is to see how leading technology companies feel an immediate affinity for Moleskine. People working for these companies use Moleskine!” Moleskine chief executive Arrigo Berni enthuses. Sebregondi adds that generally speaking, digital partners eagerly seek out Moleskine, an interesting contrast in an era when some traditional brands struggle to find a niche or build cross-platform in the digital marketplace.

That Moleskine is so sought after by big-name tech companies has a lot to do with the brand’s real and perceived worth. Moleskine’s classic notebook retails for $9.95. Limited edition journals, the first of which marked the 40th anniversary of Woodstock in 2009, are priced upwards of $18.95. Accessories like messenger bags range from $69.95 up to $220. At those price points, Moleskine falls into a luxury rubric that features brands like Starbucks (SBUX) or Swatch, brands known not just for their coffee or wristwatches but also conferring symbolic status.

The brand’s appeal isn’t completely determined by price tag. Sebregondi says that if there’s a larger misconception about the Moleskine brand, it has to do with that intangible quality that draws in passionate users, whose fandom bestows additional cultural cache. Berni notes, “Interestingly, we find that we do better whenever we are closest to an Apple retail store. This may come as a surprise, but it makes perfect sense when one considers that the profile of a Moleskine user is very similar to that of an Apple user.”

Moleskine’s first chapter wasn’t seamless. Sebregondi notes that when the company sought out Barnes & Noble (BKS) as a retail partner, it was tricky to convince a bookstore to sell what are essentially blank books. But Sebregondi was adamant Moleskine not be pigeonholed as simple stationery product, stocked near pencils or greeting cards. At a bookstore, where people go to discover new ideas and imagine a different world, she says Moleskine journals could meet the best public.

It’s no coincidence that Moleskine’s classic black, rectangular journals resemble today’s smartphones and tablets. When Moleskine was established in 1997, some of the first consumer laptops were hitting the market. From the beginning, the company has considered how to best interface with technology. Rather than struggle to keep up with innovation, Moleskine has contentiously considered how its most passionate fans and loyal customers rely on both analog and digital tools.

After conducting consumer research between 2009 and 2010, Moleskine introduced bags and pens in 2011. “I [learned] a lot about brand extensions in my years with Procter & Gamble and Bulgari. Since the beginning of my association with Moleskine, in 2006, I believed in the possibility to extend the brand into new categories, like Montblanc has done, for example,” Berni explains.

As the company has dramatically expanded its product offerings, Sebrgondi saw the writing on the wall. The need for standalone brick-and-mortar storefronts and transit station kiosks was evident. As of August 2014, Moleskine directly operates 30 stores around the world, 13 of them in China and the rest in high-traffic hubs like New York’s Time Warner Center. By 2016, Moleskine projects there will be a total of 80 located in major intentional cities.

Perhaps the only smudge on the Moleskine business plan is its performance the past 18 months on the Milan Stock Exchange. Shares are currently trading less than 50% below IPO price. But Berni points to the recent downturn in global equity markets, combined with the fact that Moleskine has always struggled to assess its business model, if only for lack of obvious competitors or points of comparison. He’s confident the brand’s latest collaborations across platforms and brands will only enhance the brand’s long-term value and better serve its core fan base.

“Moleskine was built on the idea of providing a particular subset of the adult population with tools that would expand their creativity,” he says. “This explains why we have never perceived digital as a threat to us, but rather as the development of new tools that, just like Moleskine, would contribute to expanding the creative possibilities of our users.”

That optimism, and the company’s continued growth, demonstrated why more traditional brands might take a page from the Moleskine playbook.