Men’s drastic underrepresentation in HEED occupations (health care, early education, and domestic roles) is a vastly underresearched gendered phenomenon. Using a narrative style literature review supported by a grounded theory analysis, we synthesize recent evidence on why gendered labor segregation persists in culturally feminized forms of work using an interdisciplinary approach that joins developmental psychology with the sociology of work and employment. We propose that four structural conditions facilitate the persistence of labor segregation in feminized fields: (a) the gender stereotyping and devaluation of feminized skills, (b) the unequal gender socialization of emotional and relational skills in childhood, (c) the racialized “glass escalator” phenomenon and hostile climate issues faced by men in HEED careers, and (d) disproportionate incentivizing of research on labor segregation in feminized professions. Using developmental, feminist research to support this four-pronged approach, we propose a revision to Elliott’s theory of caring masculinities that may ultimately encourage more men and boys to sustain their interest in developing skills that are associated with femininity. (PsycInfo Database Record (c) 2022 APA, all rights reserved)