Due to the complexity of chronic conditions like the metabolic syndrome (MetS), tailored dietary approaches beyond macronutrient ratio modification may be necessary to effectively address metabolic measures. Mounting data on whole foods-based, phytochemical-abundant dietary patterns, such as the Mediterranean diet, reveal that they contain constituents, such as phytochemicals, that may be beneficial for treating MetS. The role of food-based phytochemicals on underlying mechanisms of MetS, specifically as they impact insulin signaling, has yet to be investigated thoroughly. This review discusses various dietary approaches for MetS, with a focus on certain foods and dietary phytochemicals known to impact insulin signaling.