This chapter explores how ‘looking right’—as distinct from ‘looking good’—influences labor market inequalities. It is based on a sociology of valuation and evaluation (SVE) perspective, drawing from literature in critical management and organizational studies. We provide an overview of how suitability is assessed in the labor market and how career gatekeepers make decisions. We show that appearance, with a focus on ‘the right look,’ is a crucial component in assessing suitability which informs labor market success and produces specific forms of inequalities. Our empirical case analyzes aesthetic advice given by staffing agencies on their websites. This analysis illustrates how labor market intermediaries regulate ‘looking right’ through aesthetic standards and occurs early in the hiring process. We argue that in the labor market, ‘looking right’ is as vital as ‘looking good’ because employee gatekeepers focus primarily on finding the right ‘fit’ between candidate and job. In this process, visual cues of ‘fit,’ which include, but extend beyond beauty and looking good, are crucial.