Retailing dominates the informal environment where activities occur in private and public spaces. Notwithstanding the contributions from informal retailing entrepreneurs (IRE), a paucity of research remains on the complex entrepreneur-environment exchange and in particular, the relationship between retailing entrepreneurs and the informal environment in Caribbean economies. This qualitative study aims to explore the informal retailing environment between 2003 and 2018 for informal sector start-ups in the Caribbean, specifically Barbados. Guided by Gnyawali and Fogel's Integrative Model of Entrepreneurial Environments, content analysis of newspaper articles unveiled insights about the country's environmental conditions pertaining to (a) government policies and procedures, (b) socioeconomic conditions, (c) entrepreneurial and business skills, (d) financial assistance, and (e) non-financial assistance and its impact on new enterprise creations. The study's results imply that the Barbadian IRE have not been embraced fully, which reduces the likelihood of new informal venture creations testing the market and the potential for more IRE transitioning to the formal market. Empirical findings infer that efficient market functioning requires clear policies and procedures and fewer barriers limiting people from pursuing business opportunities, making the environment more conducive to new business start-ups.
