Expectations of traditional and contemporary buildings are different in terms of thermal comfort. Traditional buildings mostly achieve comfort through passive means, without HVAC support, but old levels of thermal satisfaction do not meet today’s expectations, although their passive thermal performances are notable for contemporary building designs. In this regard, the current study tries to investigate the possibility of comparing traditional and contemporary buildings’ construction techniques to achieve thermal comfort from an architectural point of view. In other words, is it possible to achieve passive building design by considering vernacular architecture principals as a reference? Likewise, how well can architects define insulation layers in contemporary construction surfaces in hot and humid climates? To this end, a dynamic, numerical, thermal calculation case study has been modeled in Famagusta, Northern Cyprus, to answer the above-mentioned questions. A mixed-use mode benefitting free-run periods is proposed and compared with a mode providing 24 hours of air-conditioning in different scenarios using the same initial settings. Thus, different floor-to-ceiling heights, insulation placements and indoor conditions have been tested separately in both winter and summer periods. The results show that thermal comfort can be achieved in free-run periods only during a limited percentage of the year. Furthermore, although increasing building heights may lead to a rise in the free-run periods, in contemporary buildings it increases the total energy usage of the buildings between 6% and 9% in the mixed mode. Therefore, vernacular architecture strategies are proper in their own context. However, this energy usage can still be controlled and optimized by such considerations as insulation material placement. In this regard, the best envelope properties for different building functions are proposed for application in hot and humid climates.