In state-of-the-art Electroencephalography (EEG) Silver/Silver-Chloride electrodes are applied together with electrolyte gels or pastes. Their application requires extensive preparation, trained medical staff and limits measurement time and mobility. We recently proposed a novel multichannel cap system for dry EEG electrodes for mobile and out-of-the-lab EEG acquisition. During the tests with these novel polymer-based multipin dry electrodes, we observed that the quality of the recording depends on the applied normal force and resulting contact pressure. Consequently, in this paper we systematically investigate the influences of electrode-skin contact pressure and electrode substrate flexibility on interfacial impedance and perceived wearing comfort in a study on 12 volunteers. The normal force applied to the electrode was varied between the minimum required force to achieve impedances <1.3 MΩ and a maximum of 4 N, using a new force measurement applicator. We found that for a polymer shore hardness A98, with increasing normal force, the impedance decreases from 348 ± 236 kΩ and 257 ± 207 kΩ to 29 ± 14 kΩ and 23 ± 11 kΩ at frontal hairless and temporal hairy positions, respectively. Similar results were obtained for shore A90, A80 and A70. The best compromise of low and stable impedances as well as a good wearing comfort was determined for applied normal forces between 2 and 3 N using electrodes with shore A98 or A90. Our results provide the basis for improved EEG cap designs with optimal wearing comfort and recording quality for dry multipin electrodes, which will enable new fields of application for EEG.