Hot on the heels of their broken-in boat shoe collab, Sperry and New York City fashion brand Colbo have announced the second chapter in their ongoing design partnership. Just in time for the transition to cooler weather, the new drop centers on a reimagined heritage silhouette: the Sperry x Colbo Captain’s Oxford, which merges Sperry’s long-standing design legacy with Colbo’s distinctive creative vision.
This iteration updates the Captain’s Oxford, a cornerstone of the Sperry archive that dates back to the brand’s origins. As one of Paul Sperry’s original designs and Sperry’s first-ever casual shoe, introduced in 1935, the shoe holds a significant place in the brand’s history, embodying the timeless style and innovation that remains central to Sperry today. Colbo cofounder and designer Tal Silberstein took the lead in updating the classic for a modern wardrobe.
Constructed with a luxurious Horween leather upper, the Sperry x Colbo Captain’s Oxford is designed to age gracefully, developing a rich patina over time that ensures it remains versatile and comfortable for everyday use. The design draws inspiration from classic dress shoes of the 1930s and ’40s, rooted in minimalist aesthetics yet built for daily wear. While Vibram outsoles provide reliable durability, a flexible leather midsole maintains the signature foldability introduced in the first collaboration—a nod to Colbo’s intuitive focus on form and function.
“Colbo has proven to be an incredible partner for Sperry,” said Jonathan Frankel, President of Sperry, in a statement announcing the latest brand collab. “Tal and his team bring a unique point of view, creating a product that is both thoughtful and elevated, while building a community that feels authentic and connected. With this collaboration, we’re not only introducing a fresh take on one of our heritage styles, but also sharing in the energy and creativity that Colbo has cultivated around its brand.”
Silberstein echoed this sentiment, noting, “Revisiting the Captain’s Oxford felt like a natural continuation of our work with Sperry because I was drawn to the shoe’s place in Sperry’s history as their first casual style. It’s simple, timeless, and adaptable. Our goal was to honor that legacy while making a version that feels relevant for today: easy to wear, versatile, and designed to age beautifully.”
The Sperry x Colbo Captain’s Oxford retails for $350, and the heritage collaboration is available now via Colbo (online and in-store) and Sperry.com.
