In this paper, we introduce a comprehensive and versatile approach to the parametric shape optimization of oleophobic surfaces. We evaluate the performance of inverse trapezoid microstructures in terms of three objective parameters: apparent contact angle, maximum sustainable hydrostatic pressure, and mechanical robustness (Im, M.; Im, H:; Lee, J.H.; Yoon, J.B.; Choi, Y.K. A robust superhydrophobic and superoleophobic surface with inverse-trapezoidal microstructures on a large transparent flexible substrate. Soft Matter 2010, 6, 1401-1404; Im, M.; Im, H:; Lee, J.H.; Yoon, J.B.; Choi, Y.K. Analytical Modeling and Thermodynamic Analysis of Robust Superhydrophobic Surfaces with Inverse-Trapezoidal Microstructures. Langmuir 2010, 26, 17389-17397). We find that each of these parameters, if considered alone, would give trivial optima, while their interplay provides a well-defined optimal shape and aspect ratio. The inclusion of mechanical robustness in combination with conventional performance characteristics favors solutions relevant for practical applications, as mechanical stability is a critical issue not often addressed in idealized models.