Pectus carinatum (PC) is a chest deformity caused by disproportionate growth of the costal cartilages compared with the bony thoracic skeleton, pulling the sternum forwards and leading to its protrusion. Currently, the most common non-invasive treatment is external compressive bracing, by means of an orthosis. While this treatment is widely adopted, the correct magnitude of applied compressive forces remains unknown, leading to suboptimal results. Moreover, the current orthoses are not suitable to monitor the treatment. The purpose of this study is to design a force measuring system that could be directly embedded into an existing PC orthosis without relevant modifications in its construction. For that, inspired by the currently commercially available products where a solid silicone pad is used, three concepts for silicone-based sensors, two capacitive and one magnetic type, are presented and compared. Additionally, a concept of a full pipeline to capture and store the sensor data was researched. Compression tests were conducted on a calibration machine, with forces ranging from 0 N to 300 N. Local evaluation of sensors’ response in different regions was also performed. The three sensors were tested and then compared with the results of a solid silicon pad. One of the capacitive sensors presented an identical response to the solid silicon while the other two either presented poor repeatability or were too stiff, raising concerns for patient comfort. Overall, the proposed system demonstrated its potential to measure and monitor orthosis’s applied forces, corroborating its potential for clinical practice.