Grape skin and seed oil are winemaking by-products with a potential nutraceutical value. This study aimed to evaluate the effects of resveratrol-enriched grape seed oil (GSO) administration on white adipose tissue (WAT) dysfunction in obese mice. Male mice were divided into four groups (n = 10/group): the chow diet (CD) group; the high-fat diet (HFD) group was fed fat from milk cream (rich in saturated fatty acids), and the HFD-GSO and HFD-GSO+R groups were fed fat from GSO in absence or presence of resveratrol (200 mg/kg/day), respectively. Glucose tolerance, metabolic profile, and inflammatory cytokines were determined. Histological studies were carried out in WAT and brown AT, RT-qPCR and western blot were used to determine the gene and protein expression. In the setting of obesity, our results unveil a novel nutritional value for winemaking by-products by which resveratrol-enriched GSO from Vitis vinifera L. in obesogenic diets favor WAT and immunometabolic homeostasis.