<i>Objective:</i> The aim of this study was to determine, which of: body mass index (BMI), waist-to-hip ratio (WHR), waist-to-height ratio (WHtR) and waist circumference (WC) correlates best with adipokines and is, therefore, the most suitable for the assessment of insulin resistance (IR), metabolic syndrome (MS), type 2 diabetes mellitus (T2DM) and coronary heart disease (CHD) risk. <i>Subjects and Methods:</i> We studied 248 T2DM patients classified by gender, IR, MS and CHD. Fasting adiponectin, leptin, resistin, high-sensitivity C-reactive protein (CRP), insulin, glucose, IR (HOMA), and lipid profile were measured. Univariate and multivariate regression analyses were used to find the associations of these variables with each other and with IR, MS and CHD. Receiver operating characteristic (ROC) analyses were used to find the best markers of IR, MS and CHD. <i>Results:</i> There were gender differences in the correlations and associations of BMI, WHR, WHtR and WC with IR, MS and CHD; e.g. in males, WHR showed significant correlation with only resistin (r = 0.30) and leptin (r = 0.39) whereas in females, it showed significant correlations with only adiponectin (r = –0.33). In males and females WHR showed the weakest correlations with CRP and the adipokines and BMI showed the highest correlations. ROC analysis showed that the BMI had the highest diagnostic values for detection of IR, MS and CHD; WHR had the worst diagnostic value. <i>Conclusion:</i> Anthropometric indices show differences in performance and associations with adipokines, CRP, IR, MS and CHD. In patients with T2DM, BMI should be the preferred marker for risk assessment on account of its association with adipokines and diagnostic performance characteristics.