Previous comparative studies describing the transition from school to work and national patterns of labor market entry have often had to simplify the complex transition processes involved. For example, the first job after education is not easy to define if a person returns to education. In addition, most of this research has concentrated on national patterns shaped by the experiences of the majority of young people. In this paper we concentrate on a particular group of school-leavers, viz. those entitled to enroll in higher education. We describe their transition patterns from school to work, including recurrent education leading to more than one instance of labor market entry after leaving education. A comparison between Germany and the United States enables us to answer the question of how various features of the tertiary education systems influence these patterns, i.e. the number of people actually returning to education and the time it takes to finally enter the labor market. The systems of higher education in Germany and the US differ in several ways that we assume to be important for the transition patterns from school to work: (a) the mode of stratification (parallel tracks in Germany vs. consecutive tracks in the US) provides different labor-market prospects and incentives for returning to education; (b) the coordination mechanism (state-controlled vs. market-based) is decisive for the diversity of institutions and their orientation to particular target groups; (c) the degree of standardization in educational programs is important for more or less smooth transitions to the labor market. Taking into account that labor-market flexibility also differs in the two countries, we derive our main hypothesis: transition patterns from higher education to the labor market in the US are less standardized and regulated than in Germany. We expect that students attending the lower-tier institutions in the US (community colleges) will display significant differences in this respect over and against their German counterparts attending a Fachhochschule (university of applied sciences). In our empirical analyses we actually find overall differences with regard to variance in the ages at which young people leave education and enter the labor market. US students gain much more labor-market experience in the period between their initial and ultimate exit from education. Differences between lower- and higher-tier institutions are less marked than expected, both within and between the two countries.