5 Years Ago, Cuyana Reimagined the “Traditional” Work Bag. Today It’s a Celebrity-Approved Best-Seller

In 2021, when many of us were just starting to remember what a work bag looked like, Cuyana set out to reinvent the category. As return-to-office plans began to take shape and hybrid schedules blurred the definition of a commute, the brand introduced the System Tote. Five years later, the leather carryall has become one of Cuyana’s best-selling bags and a celebrity favorite, spotted on the likes of Katie Holmes and Emily Blunt. This month, the label marked the tote's half-decade anniversary with a limited-edition collection that reimagines the silhouette in five new ways.

From the outside, the original System Tote is deliberately simple: a softly structured silhouette in double-faced Italian pebbled leather, with rounded corners and little visible hardware. Its defining feature is hidden inside. A series of discreet snaps allows its wearer to add and remove Cuyana’s organizational pieces—including laptop sleeves, cases, and pouches—as well as smaller bags, turning the tote into a modular, yes, system.

“The pandemic reshaped the way women lived and worked. We had to rethink what a work bag could be altogether,” says Shilpa Shah, who co-founded Cuyana with Karla Gallardo in 2011. Rather than designing something that belonged exclusively to the office—or, conversely, to off-duty life—the pair saw an opportunity for a bag that could move between both. A shopper could carry a laptop and the day’s essentials to work in a single tote, then shed some of that cargo for lunch or happy hour drinks, with smaller pieces designed to function on their own.

“When we designed the System Tote, it was really a point of inflection in the world and in women's lives. We realized that [our customer] needed something that was a more versatile piece to serve her everyday needs, and the traditional work bag wasn't enough anymore,” echoes JoEllen Dutcher, Cuyana's head of product. “The rhythm of her days changed. Some days, she's working from home; some days, she's working from a coffee shop; some days, she's commuting. Her days became very dynamic, and we knew that we needed to create a bag that would evolve and change to serve her needs.”

That adaptability was central to the design process. “Every single detail in this bag was considered,” Dutcher says. The challenge was building ample organization into the interior without making the exterior look overly technical or bulky. The team borrowed the snaps from a gold-dot detail used in Cuyana’s apparel, before engineering them to remain hidden from exterior view. They then selected the leather: supple enough to feel relaxed for everyday wear but structured enough to hold a laptop and workday must-haves without collapsing. “We had to figure out how to create a bag with all of this internal organization and capacity and abilities, but keep the outside perfectly beautiful and clean and very classic,” she adds.

The concept resonated instantly. “It was a hit immediately out of the gate,” Dutcher says. “We sold out of several of the colors within the first couple of months. The response was really, really strong from the get-go.”

The goal wasn’t simply to sell a bag with more pockets but to bring a sense of order to their customer. “I equate it to this idea: When you walk into your closet, and it's a mess, it's the worst feeling. But then when you walk in, and everything's organized, there's no better feeling than that,” Dutcher says. “We want that to be the feeling when she opens her bag. We want her to be like, ‘Oh, everything's perfect, organized. I feel good. I can conquer my day.’”

Today, that philosophy extends well beyond the original tote. The System family has expanded into Mini, Small, East West, and zippered variations; Cuyana has also incorporated the same snap system into other bags (see the Mila Satchel). “The System Tote gave us confidence to expand beyond our elevated everyday tote bags [and] into more of an enhanced design and functionality point of view,” Dutcher says.

For Dutcher, the bag’s appeal comes from pairing function with a design that doesn’t advertise its utility too loudly. “This piece has beauty, longevity, timeless design,” she says. “I think that really resonates with [our customer].” That balance has only become more relevant as the boundaries between work and personal have further blurred. Women may still need a bag that can carry a laptop, notebook, and anything else a 9-to-5 demands, but they don’t necessarily want something that looks like it belongs exclusively at a desk. “I think people are now looking for work bags that don't necessarily look like work bags,” Dutcher says.

That may also explain why Cuyana has been embraced by celebrities, too. Earlier this year, Martha Stewart singled out the Mila as a “game changer” for traveling. In June, Holmes carried a dark-chestnut 13-inch System Tote around New York with an oversized blue button-down, wide-leg jeans, and heeled flip-flops—a decidedly off-the-clock outfit. Blunt has likewise taken the Mini System Tote beyond the office, carrying a black croc-embossed version with a turtleneck, relaxed trousers, and sneakers before a TV appearance in Los Angeles.

To Dutcher, those sightings reflect a broader change in what women expect from the category. “The work bag is something that used to be all about point A to point B. Now, women are looking for bags that are more lifestyle bags,” she says. “You can take that bag with you to cocktails, to a movie, out, to wherever after you're in between the office, and you don't feel like you're trucking around your work bag. You want something that fits your style and your life.”

Shah sees that versatility as central to its staying power. “The System Tote is beautiful, but it's also genuinely functional,” she says. “The modular system lets it adapt to whatever a woman is carrying in a given season of her life, whether that's a laptop and her essentials or a change of shoes for dinner. A great work bag should feel like it's working with you, and I think that's why women keep reaching for it.”

For the System Tote’s fifth birthday, Cuyana launched Flower, Fringe, Suede, Belted, and Croc interpretations that introduce new textures and details while keeping the original architecture intact. “The anniversary gives us a chance to reflect on everything that has made the System so enduring while also taking a new step from a design perspective,” says Shah. For longtime customers who already own the original, the new versions offered a reason to revisit it. “We wanted to give her the opportunity to participate in the birthday, too,” Dutcher says.

The way women work has continued to change since 2021. The fact that Cuyana’s answer to that upheaval has stuck around may be the strongest endorsement of the original style. “For it to still be one of our bestsellers and to still be finding new people to discover it and fall in love with, it is a testament to the design,” Dutcher says. “It's a bag that stands the test of time.”