In the past 30 years, subcultures and communities have had a huge impact on fashion. Because of the digital boom and the omnichannel perspective, the costumer journey across generations and the “supermarketization” of luxury have i influenced the rise of streetwear in runway collections. However, streetwear was originally born as a reaction against an industry in which the creators could not see themselves or their value system. This paper analyzes the perception of contemporary streetwear in Italy through the eyes of generations Baby Boomers, X, Millenials and Z; the purpose is to find out whether or not there an intergenerational notion of streetwear in Italy, or on the contrary does be-longing to a certain generation affect the perception of streetwear?