Compared to force-plates, pressure-detecting insoles have the advantage that vertical ground reaction force (vGRF) can be estimated under field rather than laboratory conditions. However, the question arises whether insoles also provide valid and reliable results compared to a force-plate (i.e., the gold standard). The study aimed to investigate the concurrent validity and test–retest reliability of pressure-detecting insoles during static and dynamic movements. Twenty-two healthy young adults (12 females) performed standing, walking, running, and jumping movements while simultaneously collecting pressure (GP MobilData WiFi, GeBioM mbH, Münster, Germany) and force (Kistler^®) data twice, 10 days apart. Concerning validity, ICC values showed excellent agreement (ICC > 0.75), irrespective of the test condition. Further, the insoles underestimated (mean bias: −4.41 to −37.15%) most of the vGRF variables. Concerning reliability, ICC values for nearly all test conditions also showed excellent agreement, and the SEM was rather low. Lastly, most of the MDC_95% values were low (≤5%). The predominantly excellent ICC values for between-devices (i.e., concurrent validity) and between-visits (i.e., test–retest reliability) comparisons suggest that the tested pressure-detecting insoles can be used under field-based conditions for a valid and reliable estimation of relevant vGRF variables during standing, walking, running, and jumping.