Background: Social distancing and mask-wearing were recommended and mandatory for people during the COVID-19 pandemic. Methods: A web-based questionnaire was disseminated through social media assessing mask type preference and COVID-19 history amongst tertiary sector services and the rates of the triad of respiratory symptoms in each mask type, along with other respiratory-related parameters. Results: Amongst 4107 participants, 63.4% of the responders, mainly women, preferred medical/surgical masks; 20.5%, mainly men, preferred cotton cloth masks; and 13.8% preferred FFP/(K)N95 masks. COVID-19 history was less common in FFP/(K)N95 compared to medical/surgical (9.2% vs. 15.6%, p < 0.001) or cloth masks (9.2% vs. 14.4%, p = 0.006). Compared to the control group (rare mask-wearing, nonsmokers and without lung conditions), those wearing one medical mask were more likely to report frequent sputum production (4.4% vs. 1.9%, p = 0.026) and frequent cough (4.4% vs. 1.6%, p = 0.013), and those wearing FFP/(K)N95 masks were more likely to report frequent cough (4.1% vs. 1.6%, p = 0.048). Compared to the control group, those preferring cotton cloth masks were more likely to report a frequent cough (7.3% vs. 1.6%, p = 0.0002), sputum production (6.3% vs. 1.9%, p = 0.003) and dyspnea (8% vs. 1.3%, p = 0.00001). Conclusions: Safe mask-wearing should be in parallel with a more personalized and social interaction approach.