The Supreme NY brand encompasses fashion and music, skateboarding, and art. This study explores streetwear subculture and Supreme NY ’s history, influence, and position within the market in a European context. The study interviewed shop owners, designers, and fashion icons in London, Berlin, Milan, Barcelona, Amsterdam, Paris, and New York to elicit their perceptions of Supreme NY and the evolution of streetwear since the late 1980s. Results reveal that study respondents were significantly influenced by emerging music and skateboard culture in New York City during the 1980s and 1990s. Due to the so-called information age and rising number of new brands and collaborative projects, the streetwear industry is experiencing greater online activity than storefront patronage by enthusiasts. Results suggest that streetwear may evolve into apparel with a heavier presence online than on the street due to the growing rate of e-shopping and editorials. The term streetwear was also not concretely definable and responses from interview candidates suggested that more than apparel, streetwear is a social interactionist object and connotes a state of mind rather than a style of dress.