This study examines the iconographic transformation of the Gathering of Senior Officials (耆英會圖) painting subject from the late Koryŏ dynasty to the early Chosŏn dynasty by analyzing examples from the perspective of changing modes of self-representation among retired officials (kiro, 耆老).In the late Koryŏ dynasty, retired officials tended to represent themselves as recluses engaged in various literati activities in commemorative paintings of their gatherings. However, these idealized scenes of retirement revealed a discrepancy between representation and reality, as these individuals continued to participate in governmental affairs. During the early Chosŏn period, the gatherings of retired officials began to receive institutional support from the state. Yet they were criticized by younger officials for retaining the character of private assemblies. Thus, it is highly likely that a demand emerged for new modes of commemoration that could justify the legitimacy of such gatherings as public events.The Paintings of Gathering of Senior Officials made in the reign of King Chungjong (中宗, r. 1506-1544) delivered a political message advocating the elderly elite’s key role within the court and their close relationship with the monarch through accompanied colophons and poems. Subsequently, such paintings increasingly emphasized the identity of participants as high-ranking officials under royal patronage. In extant works from the reigns of King Myŏngjong (明宗, r. 1545-1567) and King Sŏnjo (宣祖, r. 1567-1608), the political authority of elderly officials and the formal character of the event are clearly displayed through visual iconography.These developments suggest that the transformation of the Gathering of Senior Officials subject was not merely a stylistic evolution but rather the result of shifting perceptions of retired officials and the changing political significance of their gatherings.