Adverse drug events result in hospitalization of more than 1.5 million Americans each year leading to large increases in health care costs. Although researchers have shown that a large portion of these adverse drug events are preventable, most Americans admit to only reading portions of over-the-counter (OTC) labeling, and only half say they seek out information on the label for usage information when they take an OTC medication for the first time. It is important then that we carefully consider what packaging features can motivate consumers to more thoughtfully consider the use of the OTC medicine and how packaging commonality within a product family influences the correct selection of these medications. In order to understand these questions, a controlled study was conducted with sixty-four participants who were asked to complete a Short Test of Functional Health Literacy in Adults (s-TOFHLA), a medication selection questionnaire that required participants to select the appropriate medication based on a given set of symptoms, and a packaging label ratings questionnaire. Two medication brands with five different types of package designs were studied. Product family commonality metrics were used to analyze the similarity among these simulated products, and statistical analyses were performed on the selection time and accuracy data obtained. The results illustrated that variations in labeling and product family packaging design significantly impact the accuracy and efficiency of medication decision-making and thus has the potential to reduce adverse drug events made during the OTC medication selection process.