Background/Objectives: Menu calorie labeling policies aim to promote healthier eating habits, yet their effectiveness remains debated. The present study aimed to evaluate the effectiveness of two alternative qualitative labeling strategies—Physical Activity Calorie Equivalent (PACE) labels and Percent Daily Intake (PDI) pie charts—compared to the standard numeric calorie count mandated in several countries, since they have been proposed to enhance consumer comprehension and decision-making. Methods: A nationwide online survey elicited responses from N = 885 individuals living in Italy. Survey participants were randomly assigned to one of three menu conditions: (1) numeric calorie labeling only, (2) numeric calories plus PACE labels, or (3) numeric calories plus a PDI pie chart. Participants selected a three-course meal from their respective menus. Data on sociodemographic factors, dietary habits, BMI, self-assessed nutritional knowledge, and psychological traits—restrained eating (DEBQ-R) and impulsivity (SUPPS-P)—were collected. Ordinal logistic regressions assessed the impact of labeling format, gender, and nutritional knowledge on total calories ordered. Results: Neither PACE labels nor PDI pie charts significantly influenced total calorie selection compared to numeric calorie labels alone. No significant interactions emerged between labeling format and gender or nutritional knowledge. However, age, BMI, and dietary habits were strongly associated with calorie choices: older adults, individuals with restrictive diets, and those with higher restrained eating scores selected lower-calorie meals, while participants with higher BMI or frequent meat intake opted for more calorie-dense options. Conclusions: Alternative calorie labeling formats alone may be insufficient to alter food choices in online settings. Future interventions should integrate motivational and educational strategies tailored to individual traits and dietary habits, rather than relying solely on calorie presentation format.