Vans’ legendary Old Skool silhouette continues to hold its status as an icon in both music and skateboarding. To highlight this connection, the California-based brand has launched a new campaign featuring rapper and Vans ambassador Little Simz alongside skater Helena Long.

Shot in Johannesburg, South Africa, during her visit for a performance at the House of Vans, the campaign captures the essence of the “Off The Wall” spirit. Behind the camera, Fenn O’Meally—Simz’s friend and collaborator—directed the shoot, adding a personal and authentic touch to the narrative. The British rapper, who recently returned to the music scene with her single Flood, officially joined the Vans family in 2023, taking part in various initiatives, including her own Custom Slip-On collection and live performances at the brand’s most iconic locations.

At the heart of the campaign is the Premium Old Skool Music Collection, a line that bridges past and present through three capsules inspired by different musical eras and genres. Originally released in 1977 under the name Style 36, the Old Skool was the first Vans shoe to feature the iconic Sidestripe™, quickly becoming a symbol in the skateboarding and underground music scenes. The Premium version evolves this classic with modern construction, a more comfortable fit, and archival design details.

Equipped with 30% bio-based Sola Foam ADC insoles for enhanced comfort, the Premium Old Skool also stands out for its glossy sidewalls, higher foxing tape, and ‘90s-inspired retro details. Among the standout models in the collection, the Old Skool Checkerboard, worn by Little Simz, embodies the rebellious spirit that has always defined this silhouette.

To further amplify the campaign’s message, Vans has enlisted artists who embody the energy and passion of contemporary music, including The Paranoyds, Voice of Baceprot, and HiTech. Their stories and styles reflect the brand’s creative approach, reinforcing Vans’ role as a key player in streetwear and music culture.