This research paper examines the enduring influence of Ottoman architecture in Skopje, North Macedonia, through the lens of Evliya Çelebi, a prominent travel writer of the Ottoman Empire. Focusing on the 17th century, the study highlights the architectural heritage reflected in Skopje’s urban fabric, exploring the thematic foundations, planning principles, and spatial organization of notable structures. By analyzing Çelebi's “Seyahatname,” we uncover the cultural significance and imperial authority embedded in key landmarks, particularly the Kale Fortress and Yahya Pasha Mosque while comparing their historical and contemporary states. This interdisciplinary approach combines historical analysis, architectural critique, and urban studies to enrich our understanding of Skopje’s built environment and its transformation over time. Ultimately, the research contributes to the broader scholarly discourse on cross-cultural architectural influences, revealing the complex interplay between historical forces and urban development.