A number of commentators have examined Kantian beauty in regards to its political promise. According to these readings, the free play inherent to beauty is a precondition for realizing political forms that are both pluralistic and non-coercive. But what does this mean for the design of urban spaces where pluralistic and non-coercive politics are supposed to take place? In this paper I offer a reading of urban beauty via a Kantian lens. I argue that any assessment of urban beauty is, in part, an assessment of that space’s capacity to encourage the free play necessary for non-coercive politics and a rich public life. Under this formulation, Kantian free play is not only a necessary feature of any experience of beauty but also a design ethos that can meaningfully inform urban form.