Play as a behavioural domain is characterized by freedom and flexibility, which contribute to both short-term and lasting wellbeing. Children play increasingly under supervision of adults, who generally perceive rough and rebellious behaviour negatively. The paper argues that also rebelliousness is a valuable aspect of play. The psychological research literature and case studies of design are used to explore the interplay and tension between the inherently social nature of rebelliousness and its role for the emergence and consolidation of individuality in play. This perspective is then extended to designers as creators of the tools of play: toys. Several basic design techniques are presented with the aim of understanding and appreciating rebellion within play and supporting it in design for play. The paper concludes that the psychological theories and design techniques described can be of help to designers; an understanding of the needs of children to freely explore also behaviours that go against ‘good taste’ or commonly appreciated manners help designers to open up the design space to create more diverse and less stereotypical toys that support wellbeing.