Being ‘hip’ is nowadays considered a crucial source of social prestige in the fields of fashion and music which are in a state of constant flux and revaluation. Being ‘in the know’ of new developments in the cultural field has consequently been discussed as an alternative to a status hierarchy based on social class as Bourdieu described it. In-depth interviews with young people deeply involved in urban culture scenes reveal a different perspective: They dismiss following trends which is seen as shallow, boring and too easy. Instead, their central concerns are authenticity and individuality. While the participants emphasize their openness and acceptance of other people’s tastes, not submitting oneself to any set style regimes is considered admirable. Bourdieu’s concept of naturalness turns out to be a useful theoretical approach that captures the kind of authenticity that the interviewees are performing.