Prior research has indicated that greater dietary variety in a single eating episode increases caloric intake, contributing to weight gain and obesity. This study presents a novel conceptual framework for investigating dietary variety across the entire diet according to time frame (cumulative vs. daily), aggregation level (overall vs. episode-specific), and categorization level (individual foods vs. food groups). This framework is used to assess how naturally occurring dietary variety relates to weight loss among overweight/obese women enrolled in a 16-week trial to achieve weight loss. Acknowledging this is a first exploratory attempt to test such relationships using correlational analyses, the authors uncover several key findings. First, whereas cumulative overall variety was not associated with weight loss, daily overall variety was positively associated with weight loss. Second, this relationship was strongest for variety during breakfast and afternoon snacks and was particularly driven by consuming greater vegetable variety. Overall, the authors develop a novel conceptual framework for investigating variety, and through application to a unique data set, uncover novel findings countering some existing theories about how dietary variety relates to weight loss success.