Background: The increase in serving sizes of energy-dense nutrient-poor discretionary foods over time, with attractively presented large servings and package sizes, has led to portion distortion and a new ‘normal’ for serving sizes. Little data exists on the variations of portion size norms of discretionary foods across settings. This study aimed to examine the differences in the range of normal portion sizes of commonly consumed foods between home and out-of-home settings (coffee shops, restaurants). Methods: A repeated cross-sectional design was used, with nine selected discretionary foods and beverages included in a validated online image-series questionnaire. Participants completed the questionnaire at two time points to report their normal portion sizes in home and out-of-home settings. Quantile regression models were used to examine differences in the range of normal portion sizes (17th to 83rd percentile, representing the majority of the study population) between settings. Results: A final sample of 295 participants was included in the analysis (51% females, mean age 40 ± 14 years). The ranges of normal portion sizes did not differ by settings for all test foods except for sugar-sweetened beverages (SSB) tested in both containers and glassware. SSB showed smaller normal portion sizes at home compared to fast food restaurants (in a bottle/can and in a glass/cup; p < 0.001). Conclusions: These findings suggest that the portion size norms of many discretionary foods are mostly consistent in home and out-of-home settings. As the typical serving sizes available to consumers in the out-of-home settings are large, it is essential to establish practical serving size guidelines directed at the food industry to increase the availability of smaller size options and empower consumers towards better portion control.