Superoleophobic surfaces display contact angels >150 degrees with liquids that have lower surface energies than does water. The design of superoleophobic surfaces requires an understanding of the effect of the geometrical shape of etched silicon surfaces on the contact angle and hysteresis observed when different liquids are brought into contact with these surfaces. This study used liquid-based metal-assisted etching and various silane treatments to create superoleophobic surfaces on a Si(111) surface. Etch conditions such as the etch time and etch solution concentration played critical roles in establishing the oleophobicity of Si(111). When compared to Young's contact angle, the apparent contact angle showed a transition from a Cassie to a Wenzel state for low-surface-energy liquids as different silane treatments were applied to the silicon surface. These results demonstrated the relationship between the re-entrant angle fetched surface structures and the contact angle transition between Cassie and Wenzel behavior on etched Si(111) surfaces.