Abnormal non-fasting (postprandial) lipid metabolism has been recognized as a significant contributor to dyslipidemia and cardiovascular disease (CVD) risk. Clinically, impaired metabolism of lipoproteins following a meal (e.g. chylomicrons) has been demonstrated in a number of chronic diseases, including obesity, insulin resistance, as well as type 1 and 2 diabetes. Given the proposed effects of dietary trans fat to contribute to a lipid profile that increases CVD risk, there has been a public health campaign in many countries to eliminate these fatty acids from the food supply. In contrast, our group has recently reported novel lipid-lowering benefits of a major naturallyoccurring trans fatty acid vaccenic acid (VA, shorthand lipid name 18:1 trans-11), in an animal model of dyslipidemia and the metabolic syndrome. Studies to date have shown that dietary supplementation of VA effectively reduces not only fasting lipids, but also postprandial triacylglycerol and chylomicron concentrations in obese JCR:LA-cp rats. Evidence from animal studies to date suggest that VA may downregulate hepatic fatty acid synthesis and directly influence lipogenesis in the intestine. The discovery of new bioactive properties of VA is supported by clinical studies which have provided increased momentum for industry applications. In this review we summarize the emerging beneficial view of natural trans fats that have distinct and differential properties compared to those synthetically produced in partially hydrogenated vegetable oils (PHVO), with a particular focus on fasting and postprandial lipid metabolism in CVD risk.