As information technology (IT) has become more common in everyday use, so too have concerns about the digital divide—unequal access to and use of IT across demographic groups and countries. Understanding the extent and causes of the digital divide is important because IT skills have become increasingly vital to individuals’ economic success. Although IT is widely available in both the United States and Japan, there are notable gender differences in its actual usage between the two countries. In the United States, the gender gap in IT use has narrowed over time, and according to some measures, women are at least as likely as men to use computers. In Japan, however, sizable gender gaps in IT use persist. The contrasting patterns of IT use in the United States and Japan reflect differences in the structure of social organizations and institutions in the two countries. Studying gender differences in IT use across countries thus requires a nuanced understanding of the institutional context under which gender inequality is generated. Using the United States and Japan as contrasting examples, this article examines how gender differences in IT use evolve from gender inequality in broader cultural settings, particularly labor market institutions.