Streetwear today is ubiquitous. A blanket statement for anything with vaguely skate and downtown origins—or simply sneakers, hoodies, flannels and graphic tees—the category permeates every facet of the clothing industry. With Supreme now worth a purported billion dollars and Virgil Abloh running Louis Vuitton menswear, it’s hard to imagine a world where streetwear and luxury fashion didn’t coexist. Although the term can be traced to 1980s staple Vision Streetwear, a series of notable releases in the early 2000s really propelled the modern notion of streetwear into the mainstream consciousness.

At the turn of the century, before ecommerce was an industry standard, the internet was not a pervasive force in streetwear. Most brands lacked online stores and many forgoed websites altogether. The industry was still community driven, with a small network of retail outlets, magazines and plain old word of mouth spreading information and driving sales. Although relegated to print and brick-and-mortar, a number of releases managed to overcome limitations and elicit the same type of excitement as today’s weekly Supreme drops. Below, we present a selection of products that due to a combination of their respective message, reception, connotation and aesthetic changed the public perception of streetwear as we know it.

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