Across time, the roles of women and men in the workforce have evolved. Crossing traditional gender barriers in occupational choice has become more commonplace, particularly for women who have seen domestic role changes interact with employment options. Data from the 1960 through 2000 decennial censuses and the 2010 American Community Survey were analyzed to determine trends in young adults’ occupational choices classified according to Holland’s occupational types and level of complexity, and to determine whether young adults have increasingly crossed traditional gender career barriers. The hypotheses were that while greater percentages of young women than young men (ages 18 to 29 years) would have been employed in the Artistic, Social, and Conventional categories in more recent decades, the differences in proportionate representation of young women and young men would have decreased from 1960 to 2010; that while there would have been greater percentages of young men than young women employed in the Realistic, Investigative, and Enterprising categories, the differences in proportionate representation of young men and young women would have decreased from 1960 to 2010; and that while young men would continue to be employed in work of higher mean cognitive complexity than young women, the difference in the complexity level of work done by young men and young women would have decreased from 1960 to 2010. The data are reported as percentages of women and men employed in occupations in the six Holland categories each decade, and the mean cognitive complexity of occupations in which women and men were employed from 1960 to 2010. Trends over time were examined by plotting the percentages of women and men employed in occupations in each of the six Holland categories and the mean cognitive complexity for occupations for women and men 1960 to 2010. In order to capture the overall change from 1960 to 2010, the following were calculated: odds of men and women being employed in each Holland occupational category, the relative odds from men to women in 1960 and 2010, the relative odds for women and men from 1960 to 2010, and the change in relative odds (ratio of relative odds) from 1960 to 2010. The results indicate that in the traditionally female-dominated areas, the difference between the representation of women and men did not decrease as a result of men entering traditionally female-dominated occupations. In the traditionally male-dominated areas, the difference between the representation of men and women did not decrease with the exception of the Enterprising area. The average cognitive complexity of occupations of women did come closer to that of men in the Realistic, Investigative, and Enterprising areas over time, but were fairly consistent with that of men in the Artistic, Social, and Conventional areas from 1960 to 2010. The information gained from this study elucidates changes in the gender composition of various types of work according to a psychological classification of occupations, aids career counselors in understanding whether the actual employment of young adults has reflected those aspirations of college students for women and men, and provides guidance as to how to shape young people’s occupational aspirations in the context of employment reality.