Dust masks are widely used to prevent the inhalation of particulate matter into the human respiratory organs in polluted air environments. The filter of a dust mask inherently obstructs the natural respiratory air flows, and this flow resistance is mainly responsible for the discomfort experienced when wearing a dust mask. In atmospheric conditions seriously contaminated with fine dust, it is recommended that common citizens wear a dust mask in their everyday lives, yet many people are reluctant to wear a dust mask owing to the discomfort experienced when wearing it for a long time. Understanding of physical reasons for the discomfort is thus crucial in designing a dust mask, but remains far from clear. This study presents a technique to quantify the wearing comfort of dust masks. By developing a respiration simulator to measure the pressure loss across a dust mask, we assessed the energy costs to overcome flow resistance when breathing through various types of dust masks. The energy cost for a single inhalation varies with the mask type in a range between 0 and 10 mJ. We compared the results with the survey results of 40 people about the wearing comfort of the dust masks, which revealed that the wearing comfort crucially depends on the energy cost required for air inhalation though the dust mask. Using the measured energy cost during inhalation as a parameter to quantify the wearing comfort, we present a comprehensive evaluation of the performance of dust masks in terms of not only the filtering performance but also the wearing comfort. Our study suggests some design principles for dust mask filters, auxiliary electric fans, and check valves.