The World Health Organization has advocated mandatory face mask usage to combat the spread of COVID-19, with multilayer masks recommended for enhanced protection. However, this recommendation has not been widely adopted, with noncompliant persons citing discomfort during prolonged usage of face masks. And yet, a scientific understanding on how face mask fabrics/garment systems affect thermophysiological comfort remains lacking. We aimed to investigate how fabric/garment properties alter the thermal and evaporative resistances responsible for thermophysiological strain. We constructed 12 different layered facemasks (D1-D5, T1-T6, Q1) with various filters using commercially available fabrics. Three approaches were employed: (1) the evaporative and thermal resistances were measured in all the test face masks using the medium size to determine the effect of fabric properties; (2) the effect of face mask size by testing close-fitted (small), fitted (medium) and loose fitted (large) face mask T-6; (3) the effect of face mask fit by donning a large size face mask T-6, both loose and tightened using thermal manikin, Newton. ANOVA test revealed that the additional N95 middle layer filter has no significant effect on the thermal resistances of all the face masks, and evaporative resistances except for face masks T-2 and T-3 (P-values<0.05) whereas size significantly affected thermal and evaporative resistances (P-values<0.05). The correlation coefficient between the air gap size and the thermal and evaporative resistance of face masks T-6 were R2 = 0.96 and 0.98, respectively. The tight fit large face mask had superior performance in the dissipation of heat and moisture from the skin (P-values <0.05). Three-layer masks incorporating filters and water-resistant and antimicrobial/antiviral finishes did not increase discomfort. Interestingly, using face masks with fitters improved user comfort, decreasing thermal and evaporative resistances in direct opposition to the preconceived notion that safer masks decrease comfort.