With the rapid technological advancements, schools and teachers have great responsibilities to educate students with regard to technological transformations. Students' ease of access to information and communications technology (ICT) tools provides ample opportunities for the development of these skills, not solely limited to schools. On the other hand, it is known that schools invest efforts to contribute to this process through their updated curricula. Studies on the development of ICT skills show that teachers' behavioral patterns also contribute to students' learning. In the current study, the effect of teacher and student characteristics on students' achievement regarding digital skills was examined together. Within the scope of the research, the characteristics of students and teachers were analyzed through two-level analysis with the data obtained from samples of the prominent countries--Finland and Korea--participating to the International Computer and Information Literacy Study. The analysis regarding the countries involved six models addressing teacher and student characteristics in different contexts. Demographic features, ICT usage purposes and affective characteristics related to ICT were added to the models related to teacher and student characteristics in sets. While gender, computer experience, socio-economic background and general ICT self-efficacy variables came to the fore at the student level, the adequacy of resources were more prominent at teacher level. Discussions were made on the results of the relevant variables in the study.