Objectives: To compare portion size (PS) estimates, perceived energy density (ED), and anticipated consumption guilt (ACG) for ‘healthier’ vs ‘standard’ foods.Methods: Three pairs of isoenergy dense (kJ/100 g) foods—‘healthier’ vs ‘standard’ cereals, drinks and coleslaws - were selected. For each food, subjects served an appropriate PS for themselves and estimated its ED. Subjects also rated their ACG about eating the food on a scale of 1 (not at all guilty) to 5 (very guilty).Results: Subjects (n186) estimated larger portions of the ‘healthier’ coleslaw than the “standard” version, and perceived all ‘healthier’ foods to be lower in ED than their ‘standard’ alternatives, despite being isoenergy dense. Higher ACG was associated with the “standard” foods. Portion estimates were generally larger than recommendations and the ED of the foods was underestimated.Conclusions: The larger portions selected for the ‘reduced fat’ food in association with lower perceived ED and ACG, suggests that such nutrition claims could be promoting inappropriate PS selection and consumption behaviour. Consumer education on appropriate portions is warranted to correct such misconceptions.