Wine is big business in the United States—with over $68 billion in 2018 retail sales (Wine Institute, 2019). The U.S. boasts over 10,000 wineries, which when combined with significant imports from across the globe, create a multitude of choices for consumers. Further complicating the purchase decision is the consumption occasion, which is the question of where and with whom wine is intended to be enjoyed. The purpose of this study is to improve the understanding of consumers’ interaction with typeface on wine labels and how that interaction impacts: (1) purchase intent in wine consumption scenarios of varying perceived risk and (2) perceptions of brand credibility. Sixteen typefaces were pretested by 106 respondents recruited through Amazon Mechanical Turk (“MTurk”), who determined Monotype Corsiva typeface was the most appropriate typeface for use on a cabernet sauvignon wine label and Impact typeface was the least appropriate. Main experiment participants (N = 154)—again recruited through MTurk—were randomly presented with one of four wine consumption occasions (home, gift, family dinner, and business dinner) and asked to select a wine bottle for purchase. The choice was between two digitally presented wine bottles—each utilizing the same fictitious brand name displayed in the typefaces selected in the pretest. Participants were also asked questions surrounding risk perceptions relative to the act of purchasing wine as well as brand credibility perceptions of the wine bottle selected in the choice experiment. Respondents selected the wine with the label displaying the most appropriate typeface—regardless of wine consumption occasion. The study’s results, however, failed to support a strong relationship between brand credibility and purchase intent. From a managerial perspective, this study’s results suggest wine companies would benefit from: (1) testing label typefaces with consumers to assess appropriateness (an apparent proxy for likeability and purchase intent) and (2) utilizing typefaces ranking high from such tests on wine labels.