How Chubbies delivers weekend vibes with AI.

Chubbies’ journey from rebellious idea to cultural phenomenon, now powered by AI

Chubbies was founded in 2011 by a group of fashion pioneers with a rebellious streak and a desire to treat every day like the weekend. Their first product was a simple yet bold creation: men’s retro short shorts of the ‘70s and ‘80s. Beyond the products, the founding friends created a brand that was more about fun than fashion.

What began as a niche idea quickly grew into a cultural phenomenon, with Chubbies becoming synonymous with weekend vibes, irreverent humor, and a community-driven approach to apparel. The brand’s loyal following isn’t just about the clothes—it’s about the experience, the camaraderie, and the laughter that Chubbies brings into their customers’ lives.

Expanding the Chubbies experience with Sierra’s AI

As Chubbies expanded, so did their ambitions. They wanted to scale their business while staying true to the unique brand personality that set them apart. This meant maintaining their playful, engaging customer experience even as they grew and diversified product lines. It wasn’t just about shorts anymore—Chubbies was becoming a full-fledged lifestyle brand, and the stakes were higher. Every touchpoint with customers had to reflect the brand’s ethos, from the first click on their website to post-purchase interactions.

Recognizing the need for cutting-edge technology to support their growth, Chubbies turned to Sierra to help them maintain the delicate balance between scalability and brand authenticity. The solution? Duncan Smuthers, an AI agent designed for customer service and built to embody the heart and soul of Chubbies.

Meet Duncan Smuthers: The AI agent that feels like a friend

Duncan Smuthers is no ordinary AI agent. Built on the Sierra platform, he’s a digital representative who doesn’t just answer questions—he does so with the wit, charm, and irreverence that Chubbies customers have come to expect. Whether he’s making a pun about poolside fashion or helping someone find the perfect fit for a weekend getaway, Duncan’s personality shines through, making every interaction feel personal and engaging.

But Duncan’s role extends far beyond just being a friendly face (or chat). Chubbies understood that clothing purchases are personal and that customers often have questions about size, fit, and style. Duncan was designed to handle these sensitive topics with empathy and care, ensuring that customers feel understood and supported, not just sold to. His ability to make customers laugh while also addressing their needs has made him an indispensable part of the Chubbies experience.

Driving business goals while keeping the fun alive

While maintaining brand personality was crucial, Chubbies also had key business objectives that their AI agent needed to support. One major focus was optimizing the returns process. Returns can be a pain point for any retailer, but Chubbies saw it as an opportunity. With Duncan, they aimed to not only streamline returns but also encourage exchanges when appropriate. Sierra’s technology allows Duncan to seamlessly guide customers through the process, offering alternatives and keeping the experience positive, even when things don't go perfectly.

Additionally, Chubbies required Duncan to be deeply integrated into their operations and systems, including Loop and Gladly. Powered by Sierra, Duncan can pull up customer histories, manage orders, and even suggest products—all in real time. This level of integration ensures that customers receive real-time, accurate, and secure support without ever feeling like they are interacting with a machine.

The future of Chubbies: Scaling with Sierra and Duncan Smuthers

Since implementing Duncan Smuthers, Chubbies has seen significant gains across the board. Customer satisfaction continues to be sky high, and the brand’s unique identity has been preserved—even enhanced—by the AI’s consistent, on-brand interactions. But for Chubbies, this is just the beginning. They’re already exploring new ways to use Sierra’s AI technology to further enhance the customer experience, from expanding Duncan’s capabilities to exploring new channels where Duncan can engage with customers.

As Chubbies continues to grow, they remain committed to the principles that got them here: a strong brand identity, a deep understanding of their customers, and a willingness to innovate. With Sierra’s AI at their side, Chubbies is poised to keep spreading joy, one pair of shorts—and one witty interaction—at a time.