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The aim of this study was to evaluate the association between indices of adiposity and 20-year cumulative incidence of type 2 diabetes (T2D) among apparently healthy adults participating in the ATTICA cohort study (2002-2022). The present analysis included data from 2000 individuals free of atherosclerotic cardiovascular disease (ASCVD) and T2D at baseline (age 43 ± 13 years; 51% women). Sociodemographic, anthropometric, lifestyle, clinical, and biochemical parameters were collected at baseline and follow-up examinations. Obesity-related anthropometric indices, in terms of total and central adiposity, along with dysfunctional adipose tissue-related indices, were measured. The 20-year cumulative incidence of T2D was 26.3% (95% CI [24.4%, 28.3%]). All indices were independently associated with the 20-year incidence of T2D, with an overall predictive accuracy of approximately 75%. With the exception of LAP (lipid accumulation product), all indices reflecting adipose tissue dysfunction demonstrated moderate discriminative accuracy for incident T2D (C-statistic varied between 0.70 and 0.80) over the 20-year follow-up period, in line with obesity-related anthropometric indices assessing total and central adiposity (C-statistic 0.70-0.80). Obesity-related anthropometric indices as well as dysfunctional adipose tissue-related indices were moderately predictive of long-term T2D onset, highlighting the complex role of increased body weight on glucose metabolism.