America experienced remarkable assimilation of the descendants of disadvantaged European immigrants who came to the United States in the early 20th Century and became part of the mainstream middle-class. In recent decades, new sociological theories have risen to try to explain the much slower process of assimilation experienced by recent immigrants. A key issue is the relationship between cultural and socioeconomic assimilation. In this work, I use data from the Beyond High School study to examine the effects of acculturation and peer and parent expectations on the higher educational aspirations and attainment of the children of immigrants relative to comparable youth of native born parents. I frame these results in the lens of Classical Assimilation Theory, Segmented Assimilation, and Immigrant Optimism Hypothesis, and find most support for the latter.