For the Reebok Freestyle, there’s few cities that are as important as New York City. As a city where sneakers are the luxury vehicles, Reebok’s OG ladies aerobics shoe quickly rose to cult status thanks to its sidewalk-stealing style and unique nickname. In light of this history, it makes perfect sense to tap Brooklyn-based DJ, model and modern day superwoman DJ Kitty Cash to represent the Freestyle’s next generation.

Originally released on September 1, 1982, the Freestyle (then just a low-top) quickly rose to prominence thanks to its straightforward and supportive athletic design and its unique, garment leather outer. As one of the first athletic shoes design specifically for ladies, it thrived through actively incorporating women into what was practically a men’s-only sneaker market. By 1983, the Freestyle Hi hit the market, and by the end of the 1980s, it became one of the most reliably successful silhouettes in Reebok’s arsenal.

But it’s not just athletic performance that made this shoe a cult favorite. Reebok’s athletic partnerships and reputation for performance footwear built a culture of female Freestyle fans, and those fans made sure to represent by repping the sneaker on the street. Known as both a sport and streetwear statement-maker, its popularity (especially in cities like NYC) ultimately helped it earn its nickname; by the 1990s, the Freestyle saw a second life as the 5411—a nod to its $49.99 price tag, plus tax. Thanks to New York-based rappers like Redman and DMX dropping references to the 5411 in their lyrics, the nickname managed to become as ubiquitous as the official one printed on the box.

In that tradition, seeing Kitty Cash in the Reebok Freestyle makes sense. A born and bred New York native and musician, she represents a modern version of the women that helped make the Freestyle a classic over the past 35 years. “I think ultimately, the Reebok Freestyle is a shoe that brings you back to that nostalgic feel of hip-hop in its beginnings,” explained Kitty Cash. “Thinking of girls with the big bamboo earrings and wearing their classic reeboks, it’s cool to look at that history and reinterpret it in my own modern way.”

Photographed in the LES—a place where art, music and style have been intersecting for decades—it’s the perfect reminder that, like NYC, Reebok and the Freestyle have secured a unique position not just as a fashion statement, but a cultural icon. ”I think about when Redman dropped a reference to the Reebok 5411’s. When an artist—whoever that may be—says something about a piece that you wear or own, it makes that item more authentic in a way,” noted Kitty Cash. “Reebok has always stayed true to what they are and what they represent. With a shoe that has history like the Freestyle, it’s great that Reebok isn’t just looking back, it’s inviting the current generation to step into their world of classics.”

Take a look at our contemporary take on this Reebok classic, and head over to Reebok to cop a pair of Freestyles for yourself.

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