One of the crucial issues designers should pay particular attention to is to take thermal comfort into consideration in order to prevent the indiscriminate loss of energy. In this naturalistic research conducted in Shiraz, Iran, an old (Vakil Bazaar) and a new market (Mollasdra Commercial Street), as one of the most crowded urban place, were chosen and examined from the perspective of thermal comfort. Using questionnaires regarding the times when there is sunshine and shade, 120 shopkeepers and customers of two case studies were surveyed, and by employing Ecotect Analysis 2011 the surfaces with shade and sunshine in winter and summer were simulated. The results indicate 73.3% of Mollasadra street customers are dissatisfied with existing shade especially in the summer afternoon, and 93.3% of shopkeepers use cooling and heating equipment because of congruently of orientation and quality in sunshades with climate it showed a sharp contrast with the results obtained from Bazaar Vakil in which the customers were shopping with ease most of the times thanks to its roof. At the end, in order to reach thermal comfort and resolve the problem of Mollasadra Street, some suggestion have been proposed.