Many natural surfaces contain microstructures that are used to repel liquid. However, the effects of elasticity on liquid repellency have not been thoroughly investigated. A polydimethylsiloxane (PDMS) molding process was used to create microstructured superhydrophobic surfaces of varying elasticities and geometries. These surfaces were characterized using a sliding angle test in order to measure their liquid repellency. Overall, the results show that increasing the solid fraction results in poorer liquid repellency, for elasticities ranging from 1.18 MPa to 2.86 MPa. Additionally, some results suggest that increasing the Young’s modulus of the micropillars also results in a higher degree of pinning due to a greater amount of energy consumed by pillar deformation.