The market for wearable fitness technology has grown exponentially in recent years, with an abundance of trackers available ranging from step counters to all-encompassing Smart Watches. This wealth of wearables presents an opportunity to tackle the growing rates of physical inactivity and sedentary behaviour by altering the health and physical activity behaviours that users engage in through the psychological processes embedded within wearables. The present study aimed to explore these processes, their effectiveness, and how to increase their impact upon health and physical activity behaviours by investigating user’s experiences and perceptions of wearables. This involved 11 participants who had purchased watches of their volition, or were provided one for the study undergoing a series of interviews, questionnaires and activity tracking. The findings, which though measured in their support of previous research and the influence of wearables, do illuminate a tool if honed can facilitate positive behaviour change.