If you were scrolling Tumblr or checking Hypebeast in 2011, you couldn't escape it. That grainy "Purple Swag" video dropped and suddenly everyone was obsessed with a skinny kid from Harlem who didn't dress like a rapper. Or, at least, not the kind of rapper we were used to. A$AP Rocky wasn't just wearing Supreme or BAPE. He was rocking $500 Jeremy Scott sneakers with wings on them.
It was a weird time. Hip-hop was just starting to move away from the baggy era, and Rocky was leading the charge into what people called "Street Goth."
But the relationship between ASAP Rocky and Jeremy Scott wasn't some forced corporate marketing play. It was actually organic. Rocky was a genuine fan who used to save up his money to buy Scott’s pieces way before the fame. Honestly, he was a nerd for the archives. He could look at a stitch and tell you the season it came from.
The Sneaker That Changed Everything: JS Wings 2.0 Black Flag
The peak of this friendship happened in 2013. That's when we got the adidas Originals JS Wings 2.0 "Black Flag." If you don’t remember, these were basically a tactical, all-black version of Jeremy Scott’s famous winged shoes.
They were inspired by the artwork for Rocky’s debut album, Long. Live. A$AP. The shoes featured:
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- An all-black canvas upper (way tougher than the usual leather).
- Embroidered stars and stripes, mimicking a dark, moody American flag.
- That iconic 2.0 wing silhouette that looked like the shoes were ready for takeoff.
The release date was September 28, 2013. People lost their minds. It retailed for **$250**, which was a lot for an adidas collab back then. You’ve gotta realize, this wasn’t just a shoe. It was a bridge. It connected the "high fashion" eccentricity of Jeremy Scott—who was known for putting teddy bears and gorilla heads on shoes—with the raw, street-level energy of the A$AP Mob.
Why it was a big deal for Harlem
Harlem has always been a fashion hub, but Jeremy Scott’s stuff was risky. Rocky admitted in old interviews with Dazed and Complex that you couldn't always get away with wearing that stuff uptown. People would look at you crazy. But because Rocky and his crew were "open-minded," they kicked the door down.
By the time 2012 rolled around, you’d see kids in Harlem walking around freely in winged sneakers. The "Pretty Flacko" effect was real.
A Friendship Built on Being "Outsiders"
Rocky and Jeremy Scott first met properly on the set of a Complex cover shoot in early 2012. It was a recreation of the famous Basquiat and Andy Warhol boxing poster. It fit perfectly. Scott was the established "pop art" designer, and Rocky was the rookie phenom.
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They hit it off immediately because they both viewed clothes as art, not just "merch."
Jeremy Scott has always been a polarizing figure. Some people loved his campy, over-the-top designs for Moschino and adidas, while others thought they were "disgusting" or "childish." Rocky didn't care. He liked the "no limits" approach. He told Interview Magazine that for him, style was about having no barriers—the same way he approached his music by mixing Southern "chopped and screwed" sounds with New York lyricism.
The Legacy of the "Black Flag" Era
So, what happened? Why do we still care in 2026?
Well, look at how rappers dress now. Every major artist has a luxury brand deal. You’ve got Pharrell at Louis Vuitton and Rocky himself working with everyone from Gucci to Puma. But the ASAP Rocky and Jeremy Scott era was the blueprint for the "modern influencer."
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Beyond the Wings
It wasn't just about the sneakers. This partnership helped validate the idea that a rapper could be a "muse" for a high-end designer. Before Rocky, the relationship was usually one-way: rappers mentioned brands in songs to gain status. Rocky changed it so the brands needed him for the "cool" factor.
If you’re looking to channel that 2013 energy or understand why these two are icons, here’s how you can actually apply that "Black Flag" philosophy to your own style:
- Look for the "bridge" pieces. Don't just wear high fashion or just streetwear. Find items that mix both, like a tailored blazer with technical sneakers.
- Texture over color. The "Black Flag" shoes were all black, but they used canvas, embroidery, and matte finishes to create depth. You can look interesting without wearing bright colors if you play with materials.
- Respect the archives. Rocky knew his fashion history. If you want to stand out, stop following "drops" and start looking at older collections from the early 2010s. The resale market for original Jeremy Scott adidas is still active on sites like StockX and GOAT, though prices for "Black Flag" pairs in good condition can still hover around $400 to $600.
Basically, the Rocky and Scott era proved that being a "pretty motherfucker" wasn't about the price tag—it was about having the guts to wear wings on your feet when everyone else was wearing work boots.
To really get the full vibe of this collaboration, go back and watch the "Purple Swag" and "Peso" videos. Look at the way the clothes moved. It wasn't about being "perfect"; it was about the attitude. That's a lesson that never goes out of style.
If you're hunting for a pair of the original "Black Flag" 2.0s, make sure to check the embroidery on the stars. Fakes from that era usually have messy stitching that doesn't align with the canvas grain. Real ones are surprisingly sturdy—they were built with a "bulletproof" nylon aesthetic in mind, so even a decade later, they should hold their shape.