Recent research argues both education and skills are the key to better understanding our society. However, the literature inadequately examines the heterogeneity within/across countries, overlooking nuanced patterns of societal-level educational expansion and skills diffusion. In this paper, I examine the large-scale OECD data for 27 countries, detecting five distinctive societal clusters according to the aggregate levels of education/skills across cohorts: (1) reaching universal higher education with mid-high skills (universal escalator); (2) moving towards universal escalator with mass higher education (mass escalator); (3) improving skills with relatively limited educational expansion (mass elevator); (4) enhancing education without explicit skills development (mid-skilled travelator); and (5) emerging from low levels of education and skills. As to the determinants of these societal types, cross-national heterogeneities rather than commonalities are confirmed even within the same cluster, ranging from secondary/tertiary education to adult learning, work experience, and skills use. Nevertheless, some common patterns are observed in each cluster concerning returns to education/skills. This includes the diminishing economic value of education in “mid-skilled travelator”; intensified premia for education/skills in “mass elevator”; and insignificant changes in returns to education/skills in “universal escalator.” I argue these framework/findings illuminate the characteristics of societies, thus advancing scholarship on education, stratification, and typologies.