Superhydrophobic surfaces can be quickly formed with supramolecular materials. Incorporating low molecular weight gelators (LMWGs) with perfluorinated chains generates xerogel coatings with low surface energies and high roughness. Here we examine and compare the properties of the xerogel coatings formed with eight different LMWGs. These LMWGs all have a cyclohexyl-1,2-diamide core and and two perluorinated ponytails, whose lengths varies from three to ten carbon atoms (CF3 to CF10). Investigations of the xerogels aim to provide in-depth information on the chain length effect. LMWGs with a higher degree of fluorination (CF7 to CF10) form superhydrophobic xerogel coatings with very low surface energies. Scanning electron microscopy images of the coatings show that the aggregates of CF5 and CF7 are fibrous, while the others are crystal-like. Aggregates of CF10 are particularly small and further assemble into a porous structure on the micrometer scale. To test their stabilities, the xerogel coatings were multiply flushed with a standardized water flush test. The removal of material from the surface in these flushes was monitored by a combination of water contact angle, contact angle hysteresis and coating thickness measurements. A new method based on image processing techniques was developed to reliably determine the change of coating thickness. The CF7, CF9 and CF10 surfaces show consistent hydrophobicity and coating durability after repetitive flushing tests. The length of the perfluorinated side chains thus has a significant effect on the morphology of the deposited xerogel coatings, their roughness and thus also their hydrophobicity and mechanical durability.