Research on aesthetic labor suggests that poor women’s appearance may hinder their job prospects, yet little research has examined the institutional contexts through which they might acquire these embodied capacities. I draw on 13 months of ethnographic fieldwork at a welfare-to-work nonprofit that helps unemployed poor women through “style advice” and second-hand business attire. I examine organizational policies along with interactions between staff, volunteers, and clients to understand the extent to which – and how –cultural capital is transmitted to participants. I focus especially on the relationship between “objectified cultural capital” (professional attire, in this case) and clients’ “bodily capital,” which is bounded by the intersecting corporealities of gender, race, class, and body size. I find that, despite providing an essential service to women who need professional attire, the organization reproduces the inequalities it seeks to remedy through uneven distribution of objectified cultural capital, penalizing clients seen as “undeserving” and those with stigmatized embodiments. I use these findings to caution against romanticized understandings of philanthropic efforts to remedy social inequality, while also underscoring the importance of taking embodiment – particularly the striking social disadvantages of larger body size – into account when examining the intersections of gender, race and class.