The aim of this study is to devise strategies for alleviating pressure discomfort associated with glasses-type wearables by examining pressure sensitivity at precise landmarks on the side of the head. A total of 197 healthy participants engaged in an experiment where pressure was applied using an automated force measuring system. Tactile threshold (TT), pressure discomfort threshold (PDT), maximum pressure tolerance (MPT), and pain pressure threshold (PPT) were gauged at 16 locations on the side of the head for each participant. The use of a series of grid-type templates facilitated the localization of landmarks based on individual head shapes and sizes. Notably, the area behind the ears exhibited higher pressure thresholds, while regions where temples sit horizontally were more sensitive to pressure. Gender differences were observed at specific locations, whereas age (<
45 years old) and BMI did not exhibit any significant correlation with pressure thresholds. This research introduces an automated methodology for assessing pressure sensitivity through a high-density landmark map on the side of the head. The outcomes have significant implications for the ergonomic design of head-worn products, particularly for glasses-type wearables.