Wearing masks reduces the spread of COVID-19, but compliance with mask mandates varies across individuals, time, and space. Accurate and continuous measures of mask wearing, as well as other health-related behaviors, are important for public health policies. This article presents a novel approach to estimate mask wearing using geotagged Twitter image data from March through September, 2020 in the United States. We validate our measure using public opinion survey data and extend the analysis to investigate county-level differences in mask wearing. We find a strong association between mask mandates and mask wearing-an average increase of 20%. Moreover, this association is greatest in Republican-leaning counties. The findings have important implications for understanding how governmental policies shape and monitor citizen responses to public health crises.