There is compelling evidence that bariatric weight loss reduces cardiovascular complications; however, these still tend to be the most common cause of late death after surgical intervention. In a prospective cohort study, correlations of dietary nutrients with indexes of vascular health were sought, with emphasis on vitamin D and calcium. Clinically stable obese outpatient subjects (>60 years old, N = 44) were interviewed about dietary macro and micronutrients. Nutritional assessment targeted anthropometric and bioimpedance analysis (BIA), hematologic counts, lipid profile, glucose homeostasis, and inflammatory markers. Carotid intima-media thickness (IMT) and brachial flow-mediated dilation (FMD), along with related vascular measurements, were documented, and results were correlated by uni- and multivariate analysis, corrected for known risk factors. IMT, FMD, and also brachial basal flow were positively influenced by vitamin D (P < 0.001). Calcium appeared beneficial for brachial basal flow only (P = 0.010). No association with IMT occurred, and a negative result for FMD was elicited. Also, vitamins A and B12 were advantageous for FMD, whereas iron was deleterious for IMT. Intake of many micronutrients including calcium and vitamin D did not meet recommendations. Vitamin D displayed a beneficial profile regarding vascular health, and more attention to this nutrient should be given, especially concerning obese patients with cardiometabolic risk. Calcium exhibited less straightforward results but deserves focus as well, along with antioxidant vitamin A as well as the B-complex which were mostly deficient in this experience.