Most of the young people enrolling on modern apprenticeships in the horse racing industry are women and many hope to become jockeys. The majority of those who realise these ambitions are, however, men. This paper explores this process of attrition, focussing on gendered embodiment and its relation to the development of the bodily hexis and habitus characteristic of the racing field. We argue that women engage in the bodily labour of engenderment in a context of hostility and harassment and that they develop a contradictorily gendered habitus which brings together attributes which are culturally associated with both masculinity and femininity. In order to achieve this they subject themselves to a disciplining and punishing of the body which creates a ‘tortured’ masculinity. Female bodies are, however, ‘imprisoned’ by the workings of the habitus and, within the racing field, their bodies are read as weak, not fit for hard work and as more suited to an office (or home) than a race horse. These embodied processes and practices place them at a severe disadvantage and result in women being a very small minority of jockeys.