Obesity is an important risk factor for cardiovascular diseases (CVDs). It is crucial to understand the impact of its duration due to the more extended exposure period and the higher frequency of overweight/obesity at younger ages. In the last decade, various studies have discovered that the duration of obesity, in addition to its severity, might have an impact. Therefore, this study aimed to summarize the current literature to investigate the effect of body mass index (BMI) trajectories and overweight/obesity duration on cardiovascular outcomes. To retrieve related articles, we searched PubMed, EMBASE, Google Scholar, Web of Science, Scopus, and Cochrane electronic databases. The duration of overweight/obesity is significantly associated with CVDs, especially heart failure and atrial fibrillation. However, there are contradictory results regarding the association between coronary heart disease and stroke with the duration of obesity. Additionally, no association with peripheral vascular disease has yet to be reported. The absence of this association may be brought on by covariates or various follow-up times. Nevertheless, it seems that both stable overweight and remarkably stable obesity increase the risk of CVDs, as does both stable overweight and notably stable obesity. Metrics showing both the severity and the duration of overweight/obesity are more effective than each alone, and it is recommended to be used for assessing the risk of various CVDs. There are few studies in these areas, and studies with more extended follow-up periods, with a wide age range, while adjusting for some specific covariates, are needed.