Obesity has been associated with increased arterial stiffness. Sex-differences in arterial stiffness in obesity have been less explored. To explore sex-differences in arterial stiffness by applanation tonometry in 323 women and 225 with overweight and obesity, free of cardiovascular disease. Covariables of arterial stiffness were identified in multivariable linear regression analyses in the total cohort and separately in women and men. In the total study cohort, women had higher augmentation pressure (AP) and augmentation index (AIx), and lower carotid-femoral pulse wave velocity (cf-PWV) than men, independent of confounders (all p < 0.001). In sex-specific analyses, higher AP was associated with higher age and 24-hours systolic blood pressure (BP), and with lower heart rate in women (all p < 0.001), and with higher age and BP in men (all p < 0.001). Similarly, higher AIx was associated with higher age and BP, and lower body mass index (BMI) and heart rate in women (all p < 0.05), and with higher age in men (all p < 0.001). Higher cf-PWV correlated with higher age and BP in women (all p < 0.005), and additionally with higher heart rate and non-smoking in men (all p < 0.05). When replacing BMI with waist-hip ratio, higher waist-hip ratio was associated with higher cf-PWV in men only (p < 0.05). Among subjects with overweight and obesity, AP and AIx were higher in women, and cf-PWV was higher in men. Age and 24-hours systolic BP were the main factors associated with arterial stiffness in both sexes, while measures of adiposity had little impact on arterial stiffness.