Aim: The authors present two medically interesting portraits of the famous Croatian painter Celestin Medović, with the aim of discussing the possibilities of diagnosing bilateral blepharoptosis. Material and methods: The portraits were analyzed in accordance with the postulates of iconodiagnosis. Hypothetical causes of acquired bilateral blepharoptosis are presented from the differential-diagnostic aspect. The presence of this clinical sign was also analyzed in the works of famous European painters from the 14th to the 20th centuries and Croatian painters of the 19th and 20th centuries. Results. Ptosis in “Portrait of an Old Woman” could be aponeurotic, caused by atrophy of the muscles of the upper eyelid. The ocular form of myasthenia gravis cannot be ruled out with certainty either. Muscle-specific tyrosine kinase myasthenia gravis is a possible cause of ptosis in “Portrait of a Lady from Konavle,” especially because of the left masseter muscle atrophy. Ocular myopathy or oculopharyngeal muscle dystrophy can also be a reason for bilateral blepharoptosis in both cases. Other possible causes of blepharoptosis in the portrayed women are excluded with greater or lesser certainty. Analogous to the principles of evidence- based medicine, the conclusions of the iconodiagnostic analysis are classified into four groups: A (almost certain), B (probable), C (uncertain), D (improbable), and E (impossible). The conclusion of the presented analysis would belong to group B, which means that our observations are “probably correct,” considering that they are based solely on clinical observations without insight into historical circumstances or documents that could confirm this. Through a comparative analysis of the presence of the clinical sign of ptosis in the works of famous European painters from the 14th to the 20th centuries, we found the same in a total of 11 paintings. In the works of Croatian painters of the 19th and 20th centuries, ptosis was detected in four paintings and one bronze bust. Conclusion: This paper reminds us of the importance of knowing clinical propaedeutics, in contrast to the medicaltechnological approach prevailing today, which favors numerous, often unnecessary, procedures in the process of establishing a diagnosis. Maybe the so-called “museum visits” with the aim of improving the ability of medical students to observe clinical signs on art paintings will become part of the curriculum at Croatian universities.