The literature on cities and their planners has reference to historical appreciation of art in the city landscape and to the evolution of practical application to design elements. The ideas and works of Camillo Sitte and Frederick Olmsted are particularly significant and influential in the realm of artistic functionality in urban interventions. A subjective interpretation between the two reveals more about each planner’s object of their works. This paper attempts to describe and compare the approaches to city represented by Sitte and Olmsted and aims to balance their interpretations with their critiques of the existing city and their prescriptions for reform. To this end “practical art” is represented in terms of the several applications common to the city systems of the late nineteenth century. It is concluded that both Sitte and Olmsted were moving toward developments that celebrate the quality of urban spaces, but differed in their approaches to represent the aesthetic beauty as a part of the city’s fabric.