Every now and then, a sneaker arrives that refuses to fit neatly into a single category. The Vans Old Skool 36 “Souvenir” is one of them — pulling direct inspiration from Chanel’s cult-classic 2015 On the Pavements Messenger (aka the Graffiti Bag), a rare piece famously worn by rappers Lil Yachty and Central Cee, to create a silhouette that exists at the crossroads of skate culture, streetwear, music, and high fashion.

Born in California’s skate scene, Vans has long been the uniform of rebels, musicians, and those who carve their own paths. Chanel, in contrast, is the epitome of Parisian refinement, structured, polished, and timeless. On paper, they are worlds apart. But in practice? The Souvenir Old Skool proves rebellion and refinement can share the same canvas.

When the bag debuted under Karl Lagerfeld in 2015, it sparked conversation. Paying thousands for a canvas messenger splashed with graffiti, enamel pins, and frayed tweed shocked luxury purists. But that was the point. It blurred the line between street and couture, between authenticity and aspiration. Fast forward ten years, and Vans has reimagined that same ethos through a skate lens, turning a once-divisive luxury statement into something both accessible and subversive.

“The main design inspiration was centered around the idea of traveling — what you’d see while traveling to certain places, what you’d wear while traveling to these destinations, and what you’d take home with you,” says designer Greg Betty. “For this shoe, I wanted to make something that signified the end of a long journey — like a stamped-up passport or a stickered-up Rimowa — but tied to something iconic and undeniable that multiple generations of fashion lovers would get right away. The Chanel On the Pavements Messenger Bag checked multiple boxes.”

The design details make that connection undeniable. The upper features a dirty-dyed, olive-toned canvas that feels lived-in from day one. The classic Vans jazz stripe trades clean leather for frayed, multicolor tweed, a direct nod to Chanel’s signature fabric. Scattered across the upper are enamel pins that flip Chanel’s smiley-face and yin-yang motifs through Vans’ own lens, while leather accents and metal hardware elevate the finish. It’s grungy, glamorous, and grounded all at once.

“Everything about the shoe was considered and custom-made,” Betty explains. “From the colors and thickness of the tweed, to the placement of the distressing and embroidered paint splatter, to the graphic motifs on each pin… It was truly a team effort to make sure the storytelling was felt.”

The result? A sneaker that doesn’t just borrow from Chanel, it converses with it. This is luxury filtered through skate sensibility, where imperfection becomes intentional and wear tells a story. The Souvenir isn’t a souvenir from a single trip, it’s one from decades of culture converging: skaters in Southern California, models in Paris, rappers in London, and musicians in New York all intersecting through design.

And people noticed. The Souvenir Old Skool sold out almost instantly, proving that when streetwear and luxury meet in the middle, the world pays attention. As Betty reflects, “The reception has been extremely overwhelming, beautiful, and affirming. Seeing the interest is amazing, but the discourse and educational moments that have been brought up because of this shoe has been a pleasure to witness. I think more than anything, people loved the intentionality and care behind the design.”

From a wearability standpoint, the sneaker holds up beyond its concept. The materials feel premium — sturdy canvas that softens with wear, tweed that frays with character, and enamel pins that add personality without gimmick. It fits true to size, though wide-footed wearers may prefer a half size up. This attention to quality makes it one of Vans’ most elevated offerings to date.

But what truly sets the Souvenir apart is what it represents. It’s more than a reworked Old Skool, it’s a cultural remix. In a moment where artists like Lil Yachty and Central Cee blur the line between streetwear and high fashion, Vans steps confidently into that same conversation, proving skate culture has always influenced the runway. The Souvenir isn’t chasing luxury, it’s redefining it through authenticity.

So, is it a Flex, Trade or Fade? For me, this one’s a Flex — no question. The storytelling, the craftsmanship, and the symbolism all line up. It’s a sneaker that proves fashion, music, and skate culture aren’t living in separate worlds anymore — they’re sharing the same stage. The Souvenir Old Skool doesn’t just celebrate that connection; it embodies it.

But what do you think? Would you Flex, Trade, or Fade the Vans Old Skool 36 Souvenir?