Anti-icing and anti-snow coatings are one possible strategy to mitigate ice build-up on overhead power line conductors and ground wires. The coatings are designed following different strategies, for example, using low surface energy organic or inorganic compounds or super-hydrophobic hierarchical structures. In this work, several samples of aluminum alloy conductors and guard wires were prepared with different coatings, which include commercial paints, tapes, and lab-prepared hierarchical structured surfaces. Sandblasting treatments were also performed to modulate the micro roughness of the samples, as well as different application and curing methods. The sample wettability and ice adhesion resistance were characterized through laboratory tests; hydrophobicity was tested at both room and low temperatures. Anti-snow behavior was studied by exposing the samples to real snowfall, at two sites in the Italian Alps: six dry and wet snow events were observed at temperatures close to zero Celsius. The research is conducted as part of an active collaboration with TERNA (the Italian TSO) and a number of conductor and paint manufacturers. The testing activity is important to obtain a selection of anti-icing coatings to be applied for testing on high-voltage overhead power lines exposed to the risk of wet snow. In order to visually qualify anti-icing behavior, two qualitative figures of merit are proposed. One describes the fraction of area covered by snow in a given time interval, and the second represents the maximum accretion load achieved by the sample relative to the reference. The results of the laboratory and field tests are compared and discussed. The results show that laboratory and outdoor tests are complementary and it is necessary to consider both to investigate correlations between wettability and snow behavior. Field tests indicate that several different mechanisms of snow adhesion and build-up detachment may play out depending on the structure and composition of the coating and environmental parameters.