Anti-planning thinking, characterized by reverse or non-linear problem-solving, offers a novel perspective for addressing complex challenges in urban planning. Rather than following conventional top-down planning model The study demonstrates that skyline changes are not only aesthetic markers but also reflect broader socio-economic and spatial dynamics tied to planning and construction decisions.Three main conclusions are drawn: (1) Anti-planning thinking presents significant potential in reshaping the theoretical and methodological approaches to urban planning and architectural design; (2) Quantitative studies of skylines help decode the spatial logic of urban development and enhance understanding of urban form; and (3) Changes in urban skylines are strongly influenced by planning policies and must be considered more critically in future city-making processes. These findings contribute to the evolving discourse on flexible, adaptive, and responsive urban development strategies, offering suggestions for future research directions in both theoretical exploration and practical application.