Reflecting on the Great Chicago Fire and the numerous reiterations made to improve building codes and address public needs, the article highlights how design was used to overcome and adapt to technological, physical, and societal limitations. However, design cannot always be purely utilitarian. For example, Le Corbusier’s Tower in the Park, while a functional and efficient concept, proved ineffective by Soviet block designs of towers when people were “subjected” to the design rather than being designed for. The article, thus, affirms that designs should have these three pillars, also known as the “Three-Legged Stool” model, to be good: 1) Subjectivity, 2) Contextuality, and 3) Intentionality. Subjectivity refers to the malleability and flexibility of design to address the needs of various experiences, considering how diverse identities use a space. Contextuality describes how design influences and is influenced by the physical space and metaphysical systems in which it is located – the design is made to fit. Finally, intentionality deals with designing for a better tomorrow and actively resisting harm, like hostile architecture. These pillars can also be applied when designing digital products. UX (User Experience), like cities, is effective when designed for varying users.