This essay traces a research path that reconstructs the origins of streetwear embracing a long period of time. The starting stage begins with Dapper Dan, considered the father of this line of style thanks to his interaction with hip-hop rockstars; subsequently, the focus shifts to the two cult brands of the phenomenon, represented by Stüssy andSupreme and their attention to sports like surfing and skating. The concluding part of the essay is dedicated to the figure of Virgil Abloh, who gave streetwear the impact of Marcel Duchamp’s Dadaism.