This thesis explores new ways of organising menstruation via two case studies: (i) on menstrual cup uptake among undergraduates in Melbourne, Australia, and (ii) on a pioneering menstrual workplace policy in Bristol, UK. The contemporary value given to sustainability (of products and wellbeing) made both innovations attractive within these progressively-minded, urban contexts. The usual stigma associated with menstruation was reduced, with participants speaking more openly with partners, friends, and at work about their menstrual experience. This openness sometimes involved temporary vulnerability, but also increased confidence and sense of permission to acknowledge needs. Both innovations improved workplace experience of menstruation.