Cole Bennett wears many hats. He’s a filmmaker, producer, record executive, and the founder of Lyrical Lemonade. He’s directed music videos for stars including Eminem, Justin Bieber, Drake, and J. Cole, and released his own studio album in 2024. You may not understand the hustle until you walk in his shoes. Now, you can.

After a nearly decade-long relationship with the iconic footwear brand, Bennett is collaborating with Birkenstock to reimagine the classic Boston silhouette, 50 years after its initial release in 1976. The new design pairs off-white wool with distinctive crescent moon buckles, marking a new chapter in Bennett’s relationship with Birkenstock.

“To work with this company now on a professional level is such a wild dream that has come true,” Bennett exclusively told V. “Seeing my sister wear these will be such a special moment for both of us. I still can’t believe it all.” To honor Bennett’s film career, the release of the new footwear is accompanied by a docuseries filmed between Chicago and Bennett’s hometown of Plano, Illinois. Bennett first appeared in the long-running series in 2018, exhibiting his appreciation and dedication to Birkenstock. The collaboration will also be celebrated at a dedicated panel discussion at ComplexCon. “I’ve been wearing Birkenstocks since I was a teenager,” Bennett said to V. “I know it might sound crazy, but they really became a part of my identity at some point. My sister always used to wear them growing up and I always wanted to be just like her. Once I got my first pair, I never stopped wearing Birkenstocks.”

The Boston is defined by its construction, signature silhouette, and enduring footbed. Wearability and versatility have always been central to Birkenstock, qualities that carry through Bennett’s collaboration. But his version of the Boston is also a statement piece in its own right. Inspired by ideas of transformation and innovation, the shoe demonstrates how an icon can continue to evolve. “Sometimes I touch my moon buckle if I ever need some good luck,” Bennett said. “My dog’s name is also Moon. She’s a furry mess. So in a way, this shoe is a love letter to her.”

The BIRKENSTOCK by Cole Bennett Boston launches on October 1, 2026, on 1774.com, bycolebennett.com and at selected retailers worldwide.