In many industrial and military situations it is not practical or economical to reduce ambient noise to levels that present neither a hazard to hearing nor annoyance. In these situations, personal hearing protection devices are capable of reducing the noise by 20–30 dB. Although the use of a hearing protector is recommended as a temporary solution until action is taken to control the noise, in practice, it ends up as a permanent solution in most cases. Therefore, hearing protectors must be both efficient in terms of noise attenuation and comfortable to wear. Comfort in this case is related to the agreement of the user to wear the hearing protector consistently and correctly at all times. The purpose of this paper is, firstly, to provide some background on the publications related to earmuff comfort, most of which are based on measurement of the total headband force and subjective evaluation using questionnaires. Most of the published results show a weak correlation between total headband force and subjective evaluation. Secondly, this paper presents a new method to measure the contact pressure distribution between the earmuff cushions and the circumaural flesh of the human head and estimate a comfort index. The comfort parameters were investigated and equations developed to calculate comfort indices and overall quality indices. The most important calculated comfort index is measured from the contact pressure distribution and correlated with a subjective evaluation. Measurement results for the pressure distribution of 10 earmuffs show good correlation with the subjective evaluation.