Most oil-cooled equipment like transformers are provided with radiators or heat exchangers, for the heated oil to exchange heat with the surrounding air by natural convection cooling, assisting the overall cooling process. While such radiators are effective accessories in controlling equipment temperature rise, it is ever desirable to further enhance the cooling capacity by design modifications or incorporating simplistic and cost-effective cooling technologies. In this study, computational fluid dynamic (CFD) analysis has been performed to evaluate the possibility of improving radiator performance by flow channelizing structures. Significant benefits (up to 17% increase in heat transfer coefficient) of imposing such structures, like a top chimney and an enclosure surrounding the radiator, were obtained. Although several past studies have confirmed that natural convection cooling effect can be intensified by flow channelization, the phenomenon is unique to a particular application. Given the wide variety in applications, in terms of shape, size, and structural features, it is necessary to study the effect in a given application of interest. This study points to a new direction in enhancing the cooling capacity of transformer radiators, inducing flow channelization, an easy-to-implement and cost-effective technology. Further, the study offers interesting learnings regarding flow channelization effects, which are invaluable guidelines for designers of future radiators.