Obesity and overconditioning are becoming more prevalent in horses, and are influencing the animal’s health, activity, and reproductive efficiency. Body condition score (BCS) and cresty neck score (CNS) have been correlated with the development of various diseases. Many of the papers in the literature evaluate the prevalence of obesity and overconditioning in horse populations considering BCS given by owners. The aim of this study was to evaluate the validity of the owners’ estimation of the degree of equine obesity or overconditioning by comparing BCS and CNS provided by each owner and a board-certified vet to a cohort of 259 horses and their agreement based on age, breed, sex, and activity of the animals. Overconditioning was present in 29% and 24% of horses according to the owners and the vet, respectively, and obesity in 2% and 1%, respectively. Agreement between BCS and CNS given by the owners and the vet was slight, with owners scoring horses either lower or higher than the vet. Agreement between the owners and the vet assessment was also influenced by age, breed, sex, and activity of the animals. Education of owners and caretakers to correctly assess BCS and CNS and regular evaluation of the animals throughout the year is important to prevent the development of obesity and overconditioning and related diseases.