Introduction: Chronic Venous Disease (CVD) is one of the most widespread yet institutionally underestimated conditions in contemporary healthcare. Despite its high prevalence and the significant burden it places on patients’ daily lives, it is often perceived as secondary or purely aesthetic. This tension reflects broader dynamics in the social construction of medical legitimacy, where life-threatening conditions attract institutional focus, while chronic but non-fatal illnesses remain culturally and professionally devalued. Methods: This qualitative study draws on semi-structured online interviews with 20 vascular surgeons—each representing a different Italian region—to explore how medical professionals construct and navigate the social meaning of CVD in their practice. Results: Findings illustrate a profound mismatch between the systemic complexity of CVD and its marginal status within clinical and institutional discourse. While all participants recognize the chronicity, socio-economic burden, and psychological impact of advanced CVD (e.g., venous ulcers, bleeding, etc.), they also describe it as a “Cinderella pathology”—routinely overshadowed by more acutely framed arterial diseases. Surgeons report observing different patient behaviors: arterial patients act with urgency and fear, while venous patients often display resignation or delay care. These attitudes are influenced by systemic failures, including poor public health communication, limited primary care integration, and lack of policy support for preventive and long-term care—particularly in underserved areas. Conclusions: By foregrounding the lived experiences and reflections of health professionals, this study contributes to the sociological understanding of how chronicity, medical hierarchy, and institutional inattention coalesce to shape healthcare delivery. It calls for a reconfiguration of health priorities that values everyday suffering, promotes equity, and recognizes the silent yet substantial burden of CVD within broader societal systems.