Individual respiratory protective devices and face masks represent critical tools in protecting health care workers in hospitals and clinics, and play a central role in decreasing the spread of the high-risk pandemic infection of 2019, coronavirus disease (COVID-19). The aim of the present study was to compare the facial skin temperature and the heat flow when wearing medical surgical masks to the same factors when wearing N95 respirators. A total of 20 subjects were recruited and during the evaluation, each subject was invited to wear a surgical mask or respirator for 1 h. The next day in the morning at the same hour, the same subject wore a N95 mask for 1 h with the same protocol. Infrared thermal evaluation was performed to measure the facial temperature of the perioral region and the perception ratings related to the humidity, heat, breathing difficulty, and discomfort were recorded. A significant difference in heat flow and perioral region temperature was recorded between the surgical mask and the N95 respirator ( p < 0.05). A statistically significant difference in humidity, heat, breathing difficulty, and discomfort was present between the groups. The study results suggest that N95 respirators are able to induce an increased facial skin temperature, greater discomfort and lower wearing adherence when compared to the medical surgical masks.