Learning through designing is a common pedagogical model in design education. Many design institutions utilise studio-based teaching with design tools and methods facilitating students' learning in a discovery-led way. This paper builds on the above model by examining the learning and discovery that took place that arose from a collaborative student design project named Fashion City. In contrast with most other learning models in undergraduate studio-based teaching, this project did not have a prescribed learning objective. Rather, it took an experimental approach to learn and discover from propositions, interventions, friction and failures. Instead of having a set objective, Fashion City evolved as a response to context, generated through the interactions and actions of a group of designers who all had developed research agendas. In this way Fashion City simply took a position of 'seeing what might happen' when a group of graduate students collaboratively designed a project within a particular context.