With the rise of secondary alternative schools in the Netherlands, such as Montessori and Dalton, research into its effectiveness has become crucial. Alternative schools’ greater focus on autonomy and independence may better equip students with the self-regulated learning (SRL) skills essential for higher education. The aim of this study is to investigate the transition of secondary (alternative) education to higher education. More specifically, former Dalton (N = 184), Montessori (N = 150), and regular (N = 8614) secondary education students are compared on the perceived fit between secondary education and higher education, for example in regard to learning to work together and work alone, and SRL skills in a bootstrapped hierarchical regression. Results show that former Dalton students rate the fit of their secondary education to their higher education significantly better than students who attended regular education. No other significant differences were found when comparing Montessori and regular education students regarding fit, or when comparing both Montessori and Dalton to regular education regarding the SRL skills of students. Alternative explanations regarding the differences between alternative and regular educations are discussed.