The prevalence of childhood obesity and comorbidities is rising alarmingly, and diet is an important modifiable determinant. Numerous dietary interventions in children have been developed to reduce childhood obesity and overweight rates, but their long-term effects are unsatisfactory. Stakeholders call for more personalized approaches, which require detailed dietary intake data. In the case of primary school children, caregivers are key to providing such dietary information. However, as school-aged children are not under the full supervision of one specific caregiver anymore, data are likely to be biased. Recent technological advancements provide opportunities for the role of children themselves, which would serve the overall quality of the obtained dietary data. This study aims to conduct a child-centered exploratory sequential mixed methods study to identify user requirements for a dietary assessment tool for children aged 5 to 6 years. Formative, nonsystematic narrative literature research was undertaken to delineate initial user requirements and inform prototype ideation in an expert panel workshop (n=11). This yielded 3 prototype dietary assessment tools: FoodBear (tangible piggy bank), myBear (smartphone or tablet app), and FoodCam (physical camera). All 3 prototypes were tested for usability by means of a usability task (video analyses) and user experience (This or That method) among 14 Dutch children aged 5 to 6 years (n=8, 57% boys and n=6, 43% girls). Most children were able to complete FoodBear's (11/14, 79%), myBear's (10/14, 71%), and FoodCam's (9/14, 64%) usability tasks, but all children required assistance (14/14, 100%) and most of the children encountered usability problems (13/14, 93%). Usability issues were related to food group categorization and recognition, frustrations owing to unsatisfactory functioning of (parts) of the prototypes, recall of food products, and the distinction between eating moments. No short-term differences in product preference between the 3 prototypes were observed, but autonomy, challenge, gaming elements, being tablet based, appearance, social elements, and time frame were identified as determinants of liking the product. Our results suggest that children can play a complementary role in dietary data collection to enhance the data collected by their parents. Incorporation of a training program, auditory or visual prompts, reminders and feedback, a user-friendly and intuitive interaction design, child-friendly food groups or icons, and room for children's autonomy were identified as requirements for the future development of a novel and usable dietary assessment tool for children aged 5 to 6 years. Our findings can serve as valuable guidance for ongoing innovations in the field of children's dietary assessment and the provision of personalized dietary support.