Skopje, despite its inland geographical location, maintains deep architectural, cultural, and historical connections with the Mediterranean urban fabric. This research situates Skopje’s post-1963 reconstruction, particularly its brutalist architecture, within the wider context of Mediterranean cities. These cities share traits of resilience, modernist interventions, and cultural hybridity shaping their urban development. Following the devastating earthquake, Skopje emerged as a symbol of modern architectural experimentation, guided by Kenzo Tange’s visionary masterplan that harmonized international modernist influences with local traditions. The city’s béton brut architecture—characterized by monumental forms and raw materiality—was not only an architectural response but also a socio-political statement of Yugoslavia’s modern identity. This study investigates some emblematic brutalist buildings in Skopje, exploring their spatial configurations and conceptual connections to Mediterranean principles such as the use of public space, the integration of architecture with topography, and the layering of historical and contemporary urban elements. It further examines public reception, political implications, and the tensions revealed by later interventions like “Skopje 2014.” By reading Skopje through a Mediterranean lens, its brutalist legacy emerges not merely as an episode of Yugoslav modernism but as part of a regional dialogue where tradition, modernity, and identity are continuously redefined amidst socio-political transformation.