This article explores the relationship between the cloth Harris Tweed and the cycling event, the Tweed Run. It focuses on extrapolating stories as lived and told of those participating in the event, to examine how material objects can lend agency to a fashionable cycling experience. Narrative inquiry methodology is used to explore how a subject emotionally connects with their personal possessions as revealed through storytelling. The aim is to create a new sense of meaning and significance within the research topic, rather than focusing on establishing a grand narrative. It brings specific understandings to how objects can be related to and used by individuals to become symbolic and aesthetic ‘thirds’. This study posits that it is the participatory collective nature and transformative space of events such as the Tweed Run that provide an opportunity for individuals to interact with their material objects, in a manner that supports their transformation to symbolic or aesthetic thirds and initiates satisfactory (life) stories that can advance living action.