SARS-CoV-2, the causative agent of COVID-19, which was officially declared a pandemic by the World Health Organization (WHO) on 11 March 2020, is transmitted from person to person through respiratory droplets and close contact and can cause severe respiratory failure and pneumonia. Currently, while the worldwide COVID-19 pandemic is still ongoing and countries are taking strict precautions to protect populations against infection, the most effective precautions still seem to be social distancing and wearing a mask. The question of how effective masks were in the early stages of the COVID-19 pandemic has been widely discussed, both in public and scientific circles, and the protection of different mask types has been examined. This study aimed to examine the comfort conditions provided by the different mask types to the user during use. For this purpose, single-ply, double-ply, three-ply, cloth, FFP1, FFP2, and FFP3 masks with different standards were examined, with and without a valve. To conduct the experiments, the novel thermal head measurement system, developed within the scope of this study, was used specifically for mask comfort studies. Thanks to the developed measurement system, the thermal resistance and water vapor resistance values of different masks were measured, and their comfort conditions were evaluated. According to the findings, cloth masks provide a comfortable condition, with lower thermal resistance and water vapor resistance values than other masks. In addition, it was observed that surgical masks offer better thermal comfort conditions, although they have lower protection than FFP masks.