Although obesity presents a serious health problem in children, parents often underestimate their children’s overweight and obesity status. Therefore, scientific literature was systematically screened through PubMed and PsycINFO to demonstrate the psychological, social, and cultural processes that underlie this evaluation bias. A total of 37 papers that focused on research conducted in different geopolitical contexts were taken into account. Furthermore, a lexicometric analysis of the papers’ conclusions was performed. The findings showed that education plays a key role in promoting parents’ awareness and their realistic recognition of their children’s weight. Accordingly, adequate educational support for parents should be implemented in all healthcare policies addressing childhood obesity.