This article studies an experimental pattern-cutting workshop part of a series of extension courses offered by a Brazilian University. It addresses ways in which to develop student-centred approaches to learning, highlighting the situatedness of the practitioner. In the workshop, the participants were invited to explore personal experiences as informants to their creative pattern-cutting process. The design outcomes show that experimental exercises are open to new successful encounters but also to failure, chance and disruptions. The activity is described and investigated from a participant observation viewpoint in terms of what an experimental approach to learning pattern-cutting may offer fashion design education. The results contribute to understand the roles of expectations in pattern-cutting activities, and challenges the teacher-orientation paradigm in fashion. Through these findings, the study adds to previous academic endeavours in creative pattern-cutting and fashion design education. The article concludes with a discussion on future directions for both education and practice.