This study determined the impact of undertaking an initial treatment of oak wood by sealing its surface pores with epoxy resin, focusing on the durability of transparent coating systems when exposed outdoors. Throughout the exposure period, various parameters including color, gloss, surface wettability, and both macroscopic and microscopic surface evaluation were continuously monitored. The study involved two sets of samples: one set underwent the pretreatment, while the other did not. Subsequently, four coating systems were applied to the samples, comprising two solvent-based and two water-based coatings. The experiment was conducted over a period of two years, utilizing natural weathering methods within the premises of the Czech University of Life Sciences in Prague. The pretreatment with epoxy resin exhibited enhanced durability for all paint systems. The analysis showed a significant difference in gloss and color after 12 months of weathering exposure without any significant effect on surface wettability and sealing. However, after 24 months of the weathering exposure, no significant differences between the sealed and unsealed surface were observed. The most significant change in properties was noted for the water-based coatings used in coating systems number 3 and 4, and these coatings were rated as the best.