ObjectivesDuring the COVID-19 pandemic wearing a mask in public has been recommended in some settings and mandated in others. How often this advice is followed, how well, and whether it inadvertently leads to more disease transmission opportunities due to a combination of improper use and physical distancing lapses is unknown.DesignCross-sectional observational study performed in June–August 2020.SettingEleven outdoor and indoor public settings (some with mandated mask use, some without) each in Toronto, Ontario, and in Portland, Oregon.ParticipantsAll passers-by in the study settings.Outcome measuresMask use, incorrect mask use, and number of breaches (ie, coming within 2 m of someone else where both parties were not properly masked).ResultsWe observed 36 808 persons, the majority of whom were estimated to be aged 31–65 years (49%). Two-thirds (66.7%) were wearing a mask and 13.6% of mask-wearers wore them incorrectly. Mandatory mask-use settings were overwhelmingly associated with mask use (adjusted OR 79.2; 95% CI 47.4 to 135.1). Younger age, male sex, Torontonians, and public transit or airport settings (vs in a store) were associated with lower adjusted odds of wearing a mask. Mandatory mask-use settings were associated with lower adjusted odds of mask error (OR 0.30; 95% CI 0.14 to 0.73), along with female sex and Portland subjects. Subjects aged 81+ years (vs 31–65 years) and those on public transit and at the airport (vs stores) had higher odds of mask errors. Mask-wearers had a large reduction in adjusted mean number of breaches (rate ratio (RR) 0.19; 95% CI 0.17 to 0.20). The 81+ age group had the largest association with breaches (RR 7.77; 95% CI 5.32 to 11.34).ConclusionsMandatory mask use was associated with a large increase in mask-wearing. Despite 14% of them wearing their masks incorrectly, mask users had a large reduction in the mean number of breaches (disease transmission opportunities). The elderly and transit users may warrant public health interventions aimed at improving mask use.