This doctoral thesis examines the philosophical dimensions of architecture, arguing that the persistent turpification—an unethical uglification—of the built environment undermines both individual and collective well-being. Drawing on Martin Heidegger’s concept of building as dwelling, it proposes that architecture should foster (d)well-being, a meaningful attunement of humans to their surroundings. Christian Norberg-Schulz’s genius loci (spirit of place) and Karsten Harries’ community ethos further illuminate how architecture can enhance a sense of belonging and shared identity. Since architecture is an unavoidable presence, it is inherently public and thus political—shaping human experience and influencing societal well-being. This raises a fundamental question: What constitutes well-being? Following John Finnis, this thesis argues that well-being arises from human participation in the incommensurable basic goods of human flourishing. The failure to design with this in mind has resulted in an architectural landscape dominated by uninspired, dehumanizing structures. For instance, the juxtaposition of bland boxes against Malta’s rich Baroque heritage exemplifies this crisis, where poor planning, economic greed, and short-sightedness contribute to the erosion of architectural integrity. The thesis develops an alternative model of architectural judgment inspired by analogies with legal reasoning. It argues that architecture must be practised through public reason-giving, proportionality, and fiduciary responsibility, combining professional expertise with the situated knowledge of communities. Rejecting both technocratic autonomy and rigid design codes, it proposes a model of co-responsible deliberation through which architects, policymakers, and citizens jointly interpret what places disclose and what flourishing requires. Ultimately, this thesis argues that architecture is an act of intergenerational love—an enduring gift from those who build to those who are not yet alive. A meaningful and beautiful built environment is not only a present responsibility but a legacy for future generations, shaping the world they will inherit.