It was recently unveiled that A$AP Rocky would be teaming up with Guess on a capsule collection, and at first mention, it may seem like an unlikely pairing. Guess’ relevance to youth street culture has diminished, with many probably unlikely to associate Guess with hip-hop or street culture thesedays. On the other hand, Pretty Flacko is more often considered one of the pioneers of the runway-meets-street style that developed earlier this decade (introducing the likes of likes of Rick Owens and Raf Simons to Been Trill and Black Scale fans). So why would arguably one of the hottest rappers right now and a known fashion fiend — collaborate with Guess?
Guess was a pivotal player in the fashion game in the early ’90s, with its cutting edge denim offerings establishing the market for designer jeans. Its inverted triangle logo is synonymous with style and quality execution. Slthough Guess has rebranded into something different entirely, its history cannot be ignored. Those who grew up in the ’80s or ’90s will remember Guess Jeans’ prevalence.
Guess’ popularity in the ’90s placed it on the upper echelon alongside the likes of Tommy Hilfiger and Calvin Klein. Although the jeans were more prevalent among women (led by memorable advertisements with Anna Nicole Smith), its casual yet sophisticated menswear cuts often found it styled with luxurious sportswear imprints such as Polo and Nautica.
Guess’ influence was probably biggest in New York City. Unsurprisingly, being the fashion capital of the United States, the Big Apple and its myriad of subcultures reinterpreted the Guess staples into their own looks, especially in hip-hop. Nas’ gave the brand his stamp of approval, rapping in “Represent,” “when I dress it’s never nothing less than Guess.” Andre 3000 was also a big fan, picking up the trend from the East Coast and wearing it in his native Atlanta. “You just had to be a fly boy,” according to Andre 3000. “Wear a print shirt, some Guess jeans you done dyed in the sink. Some fake Guess — sew the Guess sign on some Gap jeans.”
However, as Guess reached its peak and popularity soared, it eventually started rapidly decreasing. The turn of the century saw a new wave of streetwear led by hip-hop favorites; Ecko United, Akademics and Enyce, while Guess’ found a new target audience among young teens. Much like the decline of brands such as Tommy Hilfiger and Calvin Klein, Guess joined them in the racks at departments stores, with its ubiquity killing off its relevance.
While in the early ’90s, A$AP Rocky, aka Rakim Mayers was merely a kid growing up in Harlem, New York City, he was nonetheless right in the middle of the Guess fad. This trend, like much of one’s early memories, would play a pivotal role in Rocky’s fashion sensibility. According to his friend and stylist, Matthew Henson, “in all of my years of working, I have never met anyone with a more natural sense of style, and admiration and respect for designers than Flacko.” Fashion Killa off his 2013 record Long.Live.A$AP proves his eclectic taste for brands.
I see your Jil Sanders, Oliver Peoples/Costume National, your Ann Demeuelemeester/See Visvim be the sneaker, Lanvin or Balmain/Goyard by the trunk, her Isabel Marant/I love your Linda Farrow, I adore your Dior/Your Damir Doma, Vena Cava from the store.
Rocky’s undeniable dress-sense has gotten him attention from designers, working with Raf Simons and customizing his own adidas Originals Jeremy Scott 2.0 Wings to sitting front row at Yves Saint Laurent shows in Paris. While the A$AP Mob x PacSun collection may have been a commercial commitment frowned by the A$AP fans, the Guess collaboration is much more than a lucrative venture. Besides paying homage to ’90s fashion, Rocky, who’s never been chosen to work with a brand that fallen under the radar. Similar to how his compadre Ian Connor brought back Sketchers, there’s no denying the subtle irony at play here. Constantly pushing the boundaries to fashion, Rocky popularized androgynous label Hood by Air before disassociating himself with the brand, rapping “HBA shit is weak, you can keep that” in “Multiply.” This collaboration is another testament to his inventiveness, working outside of the public’s expectations. Currently, all we’re treated to at the moment is a red striped crewneck and triangle logo tees leaked by Rocky’s manager Chase Infinite via his Instagram. Filled with retro flair, the timing is perfect considering the resurgence in designs led by household streetwear imprints like Supreme, 10.Deep and Billionaire Boys Club. And if anyone is able to bring Guess back to its hyped heyday — it’s A$AP Rocky.
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