Organic phase change materials, e.g., paraffins, are attracting increasing attention in thermal energy storage (TES) and thermal management applications. However, they also manifest interesting optical properties such as thermotropism, as they can switch from optically opaque to transparent reversibly and promptly at the melting temperature. This work aims at exploiting this feature to produce flexible silicone-based blends with thermotropic properties for applications in glazed windows or thermal sensors. Blends are produced by adding paraffin (Tm = 44 °C, up to 10 phr) to a silicone bicomponent mixture, and, for the first time, cetyltrimethylammonium bromide (CTAB) is also added to promote paraffin dispersion and avoid its exudation. CTAB is proven effective in preventing paraffin exudation both in the solid and in the liquid state when added in a fraction above 3 phr with respect to paraffin. Rheological results show that paraffin decreases the complex viscosity, but neither paraffin nor CTAB modifies the curing behavior of silicone, which indicates uniform processability across the investigated compositions. On the other hand, paraffin causes a decrease in the stress and strain at break at 60 °C, and this effect is amplified by CTAB, which acts as a defect and stress concentrator. Conversely, at room temperature, solid paraffin only slightly impairs the mechanical properties, while CTAB increases both the elastic modulus and tensile strength, as also highlighted with ANOVA. Finally, optical transmittance results suggest that the maximum transmittance difference below and above the melting temperature (65–70 percentage points) is reached for paraffin amounts of 3 to 5 phr and a CTAB amount of max. 0.15 phr.