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“Customized,” “remixed,” “flipped” — whatever you want to call them, the story of chopped-and-screwed sneaker silhouettes is a design history as rich as it is hard to pin down. And in 2020, these homages exploded across Instagram, with DIY brands borrowing other companies’ motifs, riffing on archive silhouettes, and creating pop culture tributes to iconic shoes like the Air Jordan 1. With social media acting as a driving force, there was a sense of fun and spontaneity to the whole affair, as young creatives felt freer than ever to flip the well-known designs of established sportswear brands.

Here, streetwear galaxy brain Samuel Trotman (aka @Samutaro), along with a cadre of other laureates, takes a comprehensive look back at how things arrived to where they are today.

Sang Jordan (1985)

No shoe is knocked off more than the Air Jordan, particularly the pairs that resell for high dollar amounts. But this isn’t anything new — in fact, Jordans have been replicated from the beginning. Brands like Honors Sport and Pro-Joggs are known for their knockoff “Chicago” Air Jordan 1s from 1985. But it’s Sang’s curiously swooshed sneaker that is the rarest. Designed originally as a cheaper version of the basketball classic, even at this tier the rules of bargain alternatives still apply. A pair of Sangs can fetch up to $4,000 on resell, which still pales compared to a pair of deadstock Air Jordan 1s, which can demand up to $15,000.

PONY City Wings Jordan (1986)

These low tops earned their place in bootleg sneaker history when Spud Webb posterized the competition at the 1986 NBA Slam Dunk contest. Going back-to-back with perfect 50-point scores, Webb wowed the crowd, including one clearly gobsmacked Michael Jordan. The original style was released in a classic black, red, and white combo, which was an unmistaken take on a shoe you may very well recognize from earlier that year.

Number (N)ine Converse One Star (2001)

Fast-forwarding from the golden age of classics, the turn of the millennium saw a number of Japanese labels reimagining iconic American sneakers through clever designs that would challenge the notion of copycat shoes. One of the earliest examples of luxury bootleg styles came via Takahiro Miyashita’s Spring/Summer 2001 collection for Number (N)ine — dubbed “Time Migration.” Obsessed with punk and grunge subcultures, Miyashita reimagined Converse’s low-top One Star sneakers, famously worn by Kurt Cobain. With a satirical punk lens, he replaced the star with a skull from the “School of Visual Comedy” graphic.

BAPE Bapesta (2002)

“Nigo’s reinterpretation of the Nike Air Force 1 in the early ’00s shook the game up,” says professor of all things streetwear @Hidden.ny. “The colors, scarcity, presentation — it hadn’t been done before. The star for a Swoosh and the ape instead of air may have been small changes, but the bold patent leather, Wonderwall stores, and incredibly detailed packaging created a cult following unlike any other brand at the time. Bapestas are still celebrated for their influence decades on from their initial release. For me personally, they are what brought me into streetwear.”

Jason Dill DVS (2002)

If you look back at some of skateboarding’s most iconic silhouettes, it’s obvious that many take inspiration from original sporting styles. Think of Airwalk’s take on the Jordan for the Prototype in 1988, or Mark Gonzales and Eric Meyer’s Simple suede cupsole shoe with a leather toe cap, lifted from the Converse Chuck Taylor. By the time the 2000s came around, skaters began looking to high fashion to inspire their sneakers. In 2002, Jason Dill looked to Prada’s iconic Americas Cup as reference for his DVS pro model, which came in sleek black and brown colorways. It is a fitting choice to bite for Dill, a skater whose wardrobe consisted of a mix of skateboarding and high-fashion gear. In Alien Workshop’s seminal 2000 video, "Photosynthesis," he cops to skating in Helmut Lang pants.

Supreme Downlow (2001) and Midtown (2002)

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“Before going on to establish one of the longest and most covetable sneaker collaborations, Nike and Supreme were seemingly at loggerheads,” says vintage expert @Laughingmack. “Nike briefly pulled the plug on a Dunk link-up for its rebooted SB line in 2001, compelling the NYC brand to put out the infamous ‘Fuck Nike’ shirt, as well as their own Downlow and Midtown sneakers. Based heavily off the Nike AF1 Low and Mid respectively, the shoes also borrowed the muted solid-colorways from the renowned Nike shape, and even lifted the box design. After a deal between the two was back on the table in 2002, the first Supreme Dunk SBs were eventually realized in their now-iconic Air Jordan III-inspired form, relegating the Downlow/Midtown to streetwear history.”

Ari Menthol 10 (2006)

“The bootleg before the bootleg,” says Highsnobiety alumnus emeritus @Jiandeleon. “Ari Saal Forman’s Menthol 10s were built on a simple premise: The shoe game was an addiction that could be as debilitating as cigarettes. Ironically, Newport snuffed this collab out more than Nike, and there’s a whole documentary about the ensuing legal fallout and eventual gag order placed on Forman. Who knew Big Tobacco was much more precious about its intellectual property than Big Sneakers?”

Consolidated BS Drunks (2006)

While Nike SBs might be the de facto sneaker for young skaters today, the corporate giant wasn’t always as accepted as they are now in the skate community. One of the most vocal skate brands against the emergence of Nike into the sport was Consolidated Skateboards. The California brand went as far as producing the “BS Drunks,” copied after the Nike SB Dunk with bananas instead of Swooshes and a “Don’t Do It” motto. The satirical knock-offs are said to have been created as a backlash to Nike recruiting Consolidated designer Todd Bratrud to design a Consolidated-themed Dunk for Nike, which ended up being the “Send Helps.” Consolidated managed to shift 2,600 pairs without any legal problems.

Undercover Jack Purcell (2006)

Converse may’ve originally designed this sneaker for badminton world champ Jack Purcell in 1935, but it was grunge icon Kurt Cobain who made the shoe a cult classic in the ’90s. It was this association with Cobain that inspired Japanese UNDERCOVER designer Jun Takahashi to rework the sneaker back in 2006. Paying homage to the original black and white design, and primed with canvas uppers and thick rubber soles, Takahashi put his own stamp on the Purcell by adding his slogan “We Make Noise Not Clothes” in the shoe’s signature toe cap.

Rick Owens Dunks (2008)

“Recognized as one of Rick Owens most covetable sneakers, the Dunk is one shoe with a genuine back story,” says Rick Owens expert @Geocasket. “Rick has explained that Dunks were meant to be a parody of a number of athletic sports shoes from the era — Nike, adidas, and Puma included. The shoes are defined by their distinct ‘swoosh,’ which resembles Nike’s ubiquitous design. But rarely mentioned is the likeness it has to a vertically flipped Puma logo, with similar stitching lines. Dunks achieved grail status after Nike allegedly sent a cease and desist letter to OWENSCORP in 2008. When asked about this incident, Rick said that he ‘swooned’ and was flattered to receive the letter. Some speculate the matter was all just a cleverly crafted marketing rumor, because the sportswear behemoth never released a public statement to confirm or deny it.”

Hender Scheme Air Jordan IV (2014)

“Founded in 2010 by Ryo Kashiwazaki, Hender Scheme is a Japanese footwear and accessories label celebrated for its craftsmanship,” says Highsnobiety staffer by day and sneaker guru by night @Hartcopy. “While it has grown an impressive arsenal of original silhouettes, the brand is perhaps best known for its Manual Industrial Products (MIP) line. MIP is an ever-growing homage collection of footwear that sees classic silhouettes being remade in Hender Scheme’s signature leather, which develops a beautiful patina over time. Notable pairs include the Air Jordan IV, the Air Force 1, and the Reebok Instapump Fury. Rather than being mocked as copies, MIP sneakers are often put on a pedestal for their high quality.”

Alexander McQueen Oversized Sneaker (2016)

While bootlegs are usually associated with illicit knock-offs coming from the underground or avant-garde, Alexander McQueen creative director Sarah Jane Burton proved it could work both ways with the release of the Oversized Sneaker. Inspired by adidas’ Stan Smith tennis shoes, McQueen’s take came in buttery Italian leather and a chunkified silhouette that was still sleek enough to be worn with tailoring. First making its runway debut all the way back in 2015, the Oversized redefined the luxe trainer game by offering an upscale version of the tennis silhouette without the heaps of branding that normally come with a fashion shoe. It has been a largely unchanged bestseller for McQueen ever since.

Imran Potato Louis Vuitton AF1 (2017)

If you grew up watching hip-hop videos and reading The Source during the 2000s, then you’ll no doubt remember the Dapper Dan–esque Air Force 1s that came complete with luxury monogram fabrics. Imran Moosvi’s bootleg designs for his label, Imran Potato, pay homage to this era and have become sought after by Billie Eilish and Travis Scott alike. “Potato-ing” is Moosvi’s secret sauce, a technique that he uses to brand his deliciously warped sneakers with well-known fashion symbols.

Steve Madden Malone (2019)

While most bad bootleg sneakers got left in the mid-2000s, you can always rely on an out-of-touch designer like Steve Madden to offer up something as bad as the Malone. The high-top silhouette with dual-tone panels is almost identical to Nike’s famed Air Jordan 1, and its “Mocha Brown” colorway bears an uncanny resemblance to Travis Scott’s “Cactus Jack” AJ1.

Warren Lotas Dunks (2020)

“I’m always a fan of DIY bootleg culture,” says sneaker OG @Jeffstaple. “To me, that’s where all creativity begins. The reason why I blessed Warren Lotas’ to use the Staple Pigeon is simply because I wanted to see what would happen. What would the sneakerheads think? What would Warren’s fans think? What would Nike think? What would the culture think? It was really interesting to watch it all play out. And no matter your opinion of it, it helped redefine what’s possible. I myself have been sued by Nike while at the same time collaborating with them!”

YG 4Hunnid Block Runner “The Flame” (2021)

Shortly after Christmas, LA rapper YG offered fans a preview of merchandise from his 4Hunnid label, including a run of “The Flame” sneakers. The kicks, which are set to release this month, draw heavy influences from Nike’s ever-classic Cortez model, a silhouette that has been ingrained in West Coast hip-hop style since the late ’80s. The sneakers have received mixed response from the Internet, with some saying the shape resembles clown shoes more than the Cortez. Some also speculate YG might be in the crosshairs of a Lotas-esque lawsuit from Nike.

Experience the full story and others in HIGHStyle, a print magazine by Highsnobiety available on newsstands and the Highsnobiety shop now.

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