Recent literature has seen a growing appreciation of livelihoods based on informal artisanal and small-scale mining (ASM) that supplements women’s primary reproductive roles, leaving a gap in the parts women play at the trading end of the value chain of ASM. This paper fills that void by adding to the growing body of research on gendered trade in ASM. It focuses on women traders and the complex challenges and opportunities they face while carrying out this informal trade. The paper is based on extensive field research, interviews, and focus group discussions of women sapphire traders in southwest Madagascar, colloquially known as “ladies in hats,” who work in clan-based associations described as nascent proto-institutions. It draws upon institutional and entrepreneurial theory to understand their position in the sapphire value chain, and illuminates how women’s status could be strengthened to create the foundation for a vibrant entrepreneurial ecosystem. The paper also asks how women traders can be empowered in view of the current opportunities and challenges, and suggests that the proto-institutions could form the basis of a cooperative or a small company if regulatory and financial settings for these women can be improved and if there is an opportunity for them to formalize their trade.