Megamalls reflect the social and cultural environment, and have to a large extent, imbibe modernity attributes. It pursues the status of 'global product' and is mainly global. Often, individuals visit the megamall to search for various items at various times of the day, week, or year. Megamalls offer a secluded and easy perfect life in a city center. This study aims at understanding the underlying factors responsible for the success of mega shopping malls over small scale retail outlets in Ibadan metropolis. The study was anchored on modernization theory; a qualitative and quantitative method was combined to collect data from 222 respondents. Data were analyzed using frequency distribution tables and percentages and content analysis for the qualitative data. Findings show that megamall is increasing in Nigeria, but existing small shops languish in low patronage and sales. Their appearance in the city's structure has attracted people's attention in terms of resemblance in urban centers with social relations in a different organisation that embraces modern life components. It was also found that the essence of megamall originated from the variable choices of people, the growth of residential locations, household income increased, increased acquaintance to different lifestyles, improved consumer aspirations, double-income families, conducive and serene environment. Also, safety and a secure environment, an exhibition of ostentatious lifestyles, friendly customer care services, and one-stop shopping are the major factors underlying megamalls' success over small shops in the Ibadan metropolis. Ultimately, this study shows that megamalls are subsuming small shops retailing every standard and measure with every tool and strategy at their disposal. Therefore, it was recommended that there is a need for more megamalls as it provides people with convenient purchasing, beautifying the environment, and booming the economy without neglecting adequate grants, loans, and other necessary supports for small shop retailing systems. This will contribute immensely to society's sustainable development and boost the economy locally