Changes across education, employment, and family life over the past 20 years challenges the capacity of previously established social role combinations to continue representing the experiences of young men and women born since the late 1980s. Latent class analysis was used to derive patterns of role combinations at ages 25–26 in those growing up in England, using data from 3191 men and 3921 women in the 1970 British Cohort Study (1996) and 3426 men and 4281 women in the Next Steps study born in 1989–90 (2015–16). Role combinations in 1996 were well defined by five patterns across genders: educated, work-oriented, traditional family, fragile family, and slow starters. Patterns in 2015–16 diverged across genders (e.g., disappearance of home ownership in the traditional family group among men and higher education as a group identifier among women) and included across genders fewer work-oriented, more slow starters, and a new group of “left behind” who are excluded from work and relationships. Young men and women born around 1990 experienced diverging role combinations characterized by increased delays and inequalities, with fewer being able to attain the milestones traditionally associated with the transition to adulthood by the mid-20s.