Despite continued transmission of SARS-CoV-2 and sustained recommendations to wear protective face coverings, many people remained reluctant to comply throughout the early months of the pandemic. In the present study we surveyed an international cohort of participants on three different occasions from July to August, 2020 (N = 695) to examine the relative contribution of several factors in explaining variation in mask wearing behavior across a range of routine and leisure activities. We examine the role of COVID-19 prevalence, perceived risk of infection, COVID-19 related stress, demographics, time orientation, and several mask wearing attitudes and intentions. We find that COVID-19-related stress and the intention to protect oneself were reliably associated with more mask wearing across contexts, while other factors, such as anxiety caused by others’ mask wearing and the intention to wear masks to protect others, were context dependent. We discuss potential avenues for future research on possible positive and negative indirect effects of COVID-19-related stress, time orientation, and political orientation with regard to mask wearing behavior.