Previous studies in fashion design reveal that a new garment in individuals’ wardrobes can play various roles, such as causing excitement, keeping up with trends and feelings of belonging. But a new garment also raises other issues, such as the shortened life cycles of clothes and loose bonds between wearer and the worn. Motivated by these previous findings, this study proposes clothes as agents as a means to sustain deeper engagements between the wearer and the worn. In the project investigated here, ‘surprise’ is suggested as a provocative method for promoting wearer-worn relationships and raising awareness of the agency of clothes. To gain understanding of these engagements, artefacts were handed out to 23 individuals and were then discussed in a group. How can surprise, embedded in designed objects, contribute to the building of stronger and more reflexive dialogues? In this research-through-design, hints towards how to build more meaningful relationships with clothes are provided together with narrated experiences from users which aim at enlightening the research question. The paper concludes with findings on qualitative aspects of the dialogues developed between wearer-worn. It intends to contribute to methods in design research and addresses both practitioners and researchers in the field.