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Within the past few seasons, Shayne Oliver has become quite a sensation. His Hood by Air collection has been picked up by retailers including Barneys New York, Selfridges and Opening Ceremony, while it’s gained loyal fans in influencers like Kanye West, Rihanna and Drake.

This story first appeared in the March 26, 2014 issue of WWD.  Subscribe Today.

Oliver has also made indelible impressions with his two New York Fashion Week shows. For spring, he tapped rapper A$AP Rocky to open, and for fall, the muscularly androgynous dancers “vogue-ing” for guests were as statement-making as his curiously gender-bending looks.

The designer eschews the constraints of high fashion sensibilities while pushing the boundaries of streetwear. For his most recent lineup, he featured zipper-lined denim, grommeted suede and leather bombers along with whipstitched sweaters and his signature oversize printed T-shirts. “It’s meant to create a vagueness within strength,” Oliver said of his collection.

The name of the line came from a slang that he and his friends used while growing up in Brooklyn. “‘Hood by air’ meant to get fresh, get done up, be a dandy,” Oliver said. It’s an ethos that can be found within the brand’s identity. Oliver briefly attended the Fashion Institute of Technology before unofficially starting his line in 2006 with T-shirts emblazoned with the word “Hood.”

Ultimately, it was lessons learned from the streets — namely skaters — that provided him with the best fashion education. “I learned style from skaters and how to dress like a man — the new way of dressing like a man,” he said. “It’s not even about masculinity. It was about raw and powerful pieces that were abrupt styling and techniques of looking a certain way, and also what social meaning pieces have in general. Why the product is talking to you.”

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