This paper grounds in a research experience for engaging older people as co-designers of several wearable and in-house technologies. We start by describing a case study that is a pre-commercial procurement aimed at developing innovative services for the welfare of citizens, with a focus on older people. We present and discuss the qualitative data gathered on the occasion of a bodystorming with two groups of participants. The analysis led to the identification of the “aesthetic appropriateness”, the “social sensitivity”, and the “gender awareness” as three different dimensions that affected the acceptability of the technological devices. This approach created the conditions for instantiating the subversive power of participation. At the same time, such a subversion proved the authenticity of the participatory process. By drawing on this project, the purpose of the paper is to further our understanding of the conditions for Participatory Design.