Recently, dielectric elastomers (DEs) become enviable materials for the applications of electromechanical transducers. However, requirements of enhanced properties like high dielectric constants, low elastic moduli, high stretchability, and minimum viscous and dielectric losses are major challenges for actuator and generator applications. To enhance dielectric properties, particle‐filled DE can be prepared in the presence of an electric field during the curing process, which leads to aligned particles in a regular fashion. In this work, we develop a holistic experimental characterization approach to assess how particle alignments enhance mechanical, electrical and electro‐mechanical properties over the randomly particle filled composites. For that, a commercially available silicone polymer (Ecoflex) is used and filled with high dielectric constant barium titanate fillers. In order to substantiate electromechanical performance enhancements, mechanical, electrical, electro‐mechanical, and morphology experiments are conducted on both types of silicone composites. Dielectric composites prepared under an electric field during curing process outperform in almost all aspects of electromechanical tests. This comprehensive study provides a framework that will guide future dielectric composite preparations and electrical, mechanical, and electromechanical experiments especially for the oriented dipole fillers prepared under an electric field.