Choice set size has implications on how people select typefaces, which are normally presented in long, alphabetical lists in programs such as Microsoft Word™. The extensive size of the choice set makes choosing a typeface a difficult task, which is unfortunate because typeface selections are highly important. Choosing the right typeface ensures that the rhetoric of the message is expressed correctly, and that confusions do not occur due to low legibility. Two ways of decreasing the choice difficulty is by reducing the number of typefaces and incorporating categories into the choice set. For these reasons, this experiment explored the effects that choice set design has on typeface selections in two studies. Study 1 examined the effect that size and categorization had on the affective response (satisfaction, difficulty, etc.) and preference for making a typeface decision. Participants reported higher satisfaction and preferred typeface choice sets that contained informative categories. Results also revealed that moderate size choice sets were associated with less difficulty, less choice overload, and higher satisfaction than large choice sets. Study 2 examined the effect that categorization had on the strategy for choosing a typeface across different document types. Participants spent more time choosing a typeface and contemplated more typefaces when using choice sets that contained categories, regardless of document type. This provides evidence that categorization lead participants to use a more optimal decision strategy, which should increase the likelihood of selecting a more optimal typeface.