The presence of face masks can significantly impact processes related to trait impressions from faces. In the present research, we focused on trait impressions from faces either wearing a mask or not by addressing how contextual factors may shape such inferences. In Study 1, we compared trait impressions from faces in a phase of the COVID-19 pandemic in which wearing masks was a normative behavior (T1) with those assessed one year later when wearing masks was far less common (T2). Results at T2 showed a reduced positivity in the trait impressions elicited by faces covered by a mask. In Study 2, it was found that trait impressions from faces were modulated by the background visual context in which the target face was embedded so that faces wearing a mask elicited more positive traits when superimposed on an indoor rather than outdoor visual context. Overall, the present studies indicate that wearing face masks may affect trait impressions from faces, but also that such impressions are highly flexible and can significantly fluctuate across time and space.