Hydrophobicity and sliding behavior of water droplets were investigated on various hydrophobic pillarlike and groove structures prepared on a silicon wafer by dicing and subsequently coating with fluoroalkylsilane. The dominant hydrophobicity mode was changed from Wenzel's mode to Cassie's mode at a smaller roughness than that expected from the calculation based on the sinusoidal surface by Johnson and Dettre. The effect of water intrusion on the microstructure due to droplet weight was revealed to be an important factor governing the water sliding angle on the surface. In a comparison of the sliding behavior of water droplets over pillarlike and groove structures, it was demonstrated that a proper design of the surface with respect to shape and extent of the three-phase line is more effective than the increase of contact angles merely by decreasing the solid−water contact area.