The Italian education system has gained prominence worldwide thanks to its pioneering history in initiating the process of mainstreaming students with disabilities, in providing educational plans tailored to students’ needs, and in the gradual broadening of the vision of inclusion as a means to guarantee quality education for all. At the same time, teacher education programs have reinvigorated their key role in preparing and supporting teachers who are inclusive of all students. Several factors over the past 50 years have been fundamental in shaping the way inclusion is perceived in the 21st century. First, the theoretical frameworks underpinning pedagogy and teaching practices have undergone a complete paradigm shift from an individualized-medical model to a biopsychosocial model, bringing about a new challenge for all stakeholders involved. Second, in line with this evolution, latest reforms and ministerial provisions in initial teacher education and continuous professional development are evidence of the change in perspective regarding the teachers’ pivotal role in promoting and facilitating inclusive practices. However, this shift has not only called for a rethinking of the teachers’ pedagogical and didactic stances. It has also entailed a reconsideration of the necessary professional competencies, understood as a complex interplay of pedagogical knowledge, values, attitudes, and skills to be able to implement effective teaching methods and strategies that favor inclusion. Thus, it has placed a heavy responsibility on teacher education institutions to ensure that current and future teachers are ready, willing, and able to face the complexity characterizing 21st-century classrooms. Italian schools have also been doing their utmost to ensure better school experiences for all their students. An array of projects, both ministerially funded and school-based schemes, have been designed and implemented to create universally functional curricula to meet all the students’ learning styles and promote inclusion. One of the most important lessons to be learned from these intricate developments and initiatives is that collaboration among all stakeholders on micro, meso, and macro levels lies at the heart of effective and sustainable inclusive education.