Structural health monitoring of civil infrastructure requires low-cost, scalable, long-term, and robust sensing technologies due to the size and complexity of the geometries under consideration. This paper investigates the durability and weatherability of a large area sensing skin engineered for civil infrastructure applications. This sensing skin is based on a soft elastomeric capacitor made of three thin layers based on an SEBS block co-polymer matrix. The inner layer is filled with titania and acts as the dielectric, while the external layers are doped with carbon black and work as the conductive plates. In this work, a variety of specimens, including the dielectric layer without the conductive plates, were fabricated and tested within an accelerated weathering chamber by simulating thermal, humidity, and UV radiation cycles. Beyond the accelerated weathering tests, a sensor deployed on a bridge in Iowa for six and a half years was removed from the field and analyzed in the laboratory. A variety of other tests were performed in order to characterize the specimens’ mechanical, thermal, optical, and electrical performance. Additionally, strain sensitivity analyses were performed on specimens of interest. Results showed that titania inclusions improved the sensor dielectric's durability against weathering, while the carbon black doped conductive layers provided the skin sensor with a high level of durability and weatherability protection. The results in this work contribute to a better understanding of the degradation of SEBS-based matrices as well as the behavior of these skin sensors when deployed for the monitoring of civil infrastructure.