This study seeks to measure teachers’ readiness to use ICT in Italy by exploiting the data collected by the National Institute for the evaluation of education and training system (INVALSI) in 2018–2019. We propose a fuzzy set approach to provide a multidimensional picture of how much teachers were ready to integrate ICTs into educational practice. In addition, we use empirical bootstrap intervals to test whether significant differences exist in teacher readiness over several personal and socioeconomic characteristics. The study reveals that teachers’ readiness for ICT is composed of three dimensions and varies by teachers’ characteristics and regions. These results are a useful tool for understanding the relationship between teachers and ICTs so as to develop more appropriate educational policies.