Since the early days of the COVID-19 Pandemic, face masks have emerged as a flashpoint of controversy in public discourse. While most Americans appreciate the public health importance of mask-wearing, some view masks as an unwanted imposition; some still, an affront to deep-seated values of individual liberty. In this paper, we present the results of an experiment aimed at assessing what effects, if any, face mask usage has on perceptions of an individual’s trustworthiness. While previous studies have used images of masked faces to elicit survey responses, this experiment used self-reported mask usage as a primer in a modified investment game to assess potential relations between mask usage and perceived trustworthiness. We find evidence to suggest individuals who report wearing masks more frequently are trusted more than individuals who report seldom wearing masks. Given the importance of trust between often-masked medical professionals and the public in the setting of infectious disease outbreaks, we believe the findings of this experiment may prove fruitful in elucidating the effects of personal protective equipment (PPE) usage on perceptions of trustworthiness.