Using elements derived from what marks a place as singular is key to contemporary placemaking, understood as a primary objective of the theory of critical regionalism. The need to create humane, remarkably local architecture and to minimize the effects of universal and international clichés, in order to avoid the danger of making architecture locally unfounded and to invest it with meaning and a sense of place, certainly poses a challenge for every modern architect. This paper deals with the issue of contextuality and approach to the character and urban matrix of a place, as characterizing the buildings in the Western Serbian city of Užice designed by architect Mihajlo Timotijević. A critical approach is adopted in analyzing Timotijević’s architectural plans and buildings constructed in Užice, in the attempt to show that the architect takes a genuine interest in the local topography and that which is called placemaking. The main goal of this research is to underline the fact that Timotijević’s ability to perceive and read the messages sent by a place, materialize its distinctivness and easily incorporate a “sense of placeˮ in architectural spaces has given the city of Užice a new image, by integrating the spirit of the regional with that of the contemporary. The research results are particularly pertinent to contemporary architectural theory and practice, both in Serbia and the region, as a comprehensive, multifaceted example of a good practice of critical regionalism.