In today's fashion system, dominated by business models predicated on continual consumption and globalized production systems that have major environmental and social impacts, the consumption of ‘sustainable fashion’ takes on an almost paradoxical quality. This paper explores this paradox by focusing on a previously under-researched group of consumers – ‘sustainable fashion consumption pioneers’ who actively engage and shape their own discourse around the notion of sustainable fashion consumption. These pioneers actively create and communicate strategies for sustainable fashion behaviour that can overcome the nebulous and somewhat paradoxical reality that sustainable development in the fashion industry presents. Specifically, we use passive netnography and semi-structured interviews to illuminate the role of motivational and contextual factors that help shape these consumers' definitions of sustainable fashion including such key behaviours as purchasing fewer garments of higher quality, exiting the retail market, purchasing only second-hand fashion goods and sewing or upgrading their own clothing. Central to much of these behaviours is the notion that personal style, rather than fashion, can bridge the potential disconnect between sustainability and fashion while also facilitating a sense of well-being not found in traditional fashion consumption. As such, our research suggests that for these consumers sustainability is as much about reducing measurable environmental or social impacts as it is about incorporating broader concepts through which to achieve goals beyond the pro-environmental or ethical.