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This paper aims to interpret the identity paradoxes of postmodern countercultures to make them understandable and usable by brands. Taking hipster counterculture as the field of research, it attempts to answer the following question: How do brands convert the counterculture’s identity paradoxes into a lever for marketing action? A qualitative study of twenty-five in-depth interviews provides an understanding of the difference between the way hipsters perceive themselves, and the way they are perceived via a typology of six contradictory pairings: 1. lack of categorization vs community members; 2. marginal vs bourgeois; 3. avant-garde vs trendy; 4. free vs trapped by their codes; 5. self-taught vs apprentice; 6. passionate vs indifferent. These identity paradoxes result in management recommendations for brands wishing to target this type of consumer and more globally supporters of countercultural consumption.