Background: Several studies have investigated the factors associated with mask-wearing in adults, but very few studies have explored mask wearing in children or schools. As such, our study aims to explore the knowledge, attitudes, and psychological factors impacting mask-wearing in high school students. Methods: In February 2023, a cross-sectional survey was distributed online to Grade 9–12 students in a school located in Toronto. The association between knowledge, attitudes and psychological variables was evaluated using descriptive statistics and Kendall’s tau-b rank correlation tests. Thematic analysis was then used to summarize the qualitative responses. Results: A total of 62 participants fully completed the survey. 46.8% (n = 29) identified as male, 43.5% (n = 27) as female, and the median age was 16 years (IQR, 15–17 years). Almost all participants indicated that they were knowledgeable about COVID-19's modes of transmission (n = 57, 92.0%) and preventative measures (n = 60, 96.8%). More participants supported voluntary masking in schools (n = 34, 54.9%) compared to mask mandates (n = 16, 25.9%). Attitudes towards masking in schools, perceived susceptibility, perceived aesthetic, and anxiety-reduction benefits were positively correlated with higher frequencies of mask-wearing (τb = 0.238 to 0.491, p = 0.03 to <0.001). However, perceived barriers (e.g., physical discomfort, hindrance to communication, inconvenience) were negatively correlated (τb = -0.259 to -0.385, p = 0.0019 to <0.001). Age, sex, self-reported COVID-19 knowledge, perceived severity, and perceived medical benefits were not significant correlates of masking behaviour. Qualitative reasons that encouraged individuals to wear masks included protection and aesthetic reasons. Students who did not wear masks questioned the necessity of mask-wearing and commented on the new social norm of not wearing a mask among their classmates. Conclusion: Adolescent mask-wearing is significantly correlated with pre-existing attitudes towards masks, while perceived barriers strongly discourage students from wearing masks. Future research should investigate how to best promote positive beliefs regarding mask-wearing to youth.
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