Understanding the wettability of soft surfaces is of key importance for the development of protective and repellent coatings and controlling droplet dynamics when required. There are many factors that affect the wetting and dynamic dewetting behavior of soft surfaces, such as the formation of wetting ridges, the adaptive behavior of the surface caused by the interaction of the fluid with the surface, or the presence of free oligomers that are washed out of the soft surface. In this work, we report the fabrication and characterization of three soft polydimethylsiloxane (PDMS) surfaces with elastic moduli ranging from 7 kPa to 56 kPa. The dynamic dewetting behavior of liquids with different surface tensions was studied on these surfaces, and the data show soft and adaptive wetting behavior of the soft PDMS, as well as the presence of free oligomers. Thin layers of Parylene F (PF) were introduced to the surfaces and their influence on the wetting properties was studied. We show that the thin layers of PF prevent adaptive wetting by preventing the diffusion of liquids into the soft PDMS surfaces and by causing the loss of the soft wetting state. The dewetting properties of the soft PDMS are enhanced, leading to low sliding angles of ≤10° for water, ethylene glycol, and diiodomethane. Therefore, the introduction of a thin PF layer can be used to control wetting states and to increase the dewetting behavior of soft PDMS surfaces.