Drawing on a study of how young people in Switzerland appropriate urban public space, this article explores what we term “regimes of self-presentation” among youth in both online and offline spaces. We address issues of privacy and power that help shape such regimes by applying an expanded notion of street credibility that encompasses digital practices. Our concept of “digital street credibility” recognizes how, in today’s world, any social or cultural practices engaged in by youth have two potential types of audiences. One is physically present, consisting of other users of urban public space. The second audience is media-based, consisting of people with access to live or prerecorded digital content captured on smartphones and shared on social networks. This situation has forced young people to develop new and specific social conventions governing self-presentation. The article highlights the complex and perilous nature of visibility management. Where privacy and power relations are concerned, a very thin line separates behavior that enhances an individual’s social status from actions considered “embarrassing” or “cringe.” Our results show how, in the streets as well as online, acceptable forms of visibility are determined on the basis of digital street credibility. These findings suggest a need to reconsider young people’s understanding of privacy, as it relates to their leisure activities in urban and digital spaces.