Harris Tweed, a woollen textile that can only be produced in the Outer Hebrides of Scotland, has been trademark protected since 1910 and covered by its own Act of Parliament since 1993. According to this legislation, a tweed can only be stamped with the Orb trademark if it 'has been handwoven by the islanders at their homes in the Outer Hebrides, finished in the Outer Hebrides, and made from pure virgin wool dyed and spun in the Outer Hebrides' (1993). Despite this localised production model, the cloth is exported to over 50 countries and trademark protected in over 30. And while the emphasis on provenance might suggest that only people born and raised in the islands would be involved in its production, my research draws attention to the inclusive possibilities that the concept of 'islander' holds in this particular setting, suggesting alternative ways of thinking through notions of rootedness and belonging. Proposing an expanded concept of productive work and labour, in this thesis I foreground the active ways in which people of different origins and backgrounds navigated island life, both making a living and becoming part of its fabric by participating and elaborating on local practices and pursuing particular visions of good lives. Based on thirteen months of ethnographic fieldwork in the Isle of Lewis and Harris (the Outer Hebridean island where the Harris Tweed industry came to be concentrated), this research involved spending time learning from workers in the various workplaces where Harris Tweed is made - woollen mills, domestic loomsheds, Harris Tweed Authority offices, and tweed vans. This focus on the lives of workers, workplaces and work processes, I argue, offers a unique lens through which to examine the diversity of lived experiences and productive social processes that emerge as people variously navigate the complexities and contradictions of contemporary global capitalism. Further, I suggest, examining the workings of the Harris Tweed industry as well as its social and personal implications highlights the need to redefine an expanded concept of work / labour that accounts for the layered meanings and analytical potential it holds. In a region described as economically fragile, Harris Tweed has long offered local employment, contributing to population retention - despite its vulnerability to shifting global markets. I discuss how people's awareness of their shared circumstances as fellow islanders - facing particular regional challenges whether they were 'locals', 'returners' or 'incomers' - revealed a sense of shared precariousness and shared responsibility, highlighting particular resourceful practices and outlooks on the possibility of change. Discussing how people drew on (and reinterpreted) local histories and 'shared repertoires' as they navigated and made sense of their present and imagined futures, I highlight how inclusive notions of belonging encompassed people's active engagement with local practices and moral understandings, revealing how various kinds of work contributed to making the material and social fabric of the islands.