Despite widespread acknowledgment that entrepreneurship takes place in a broader societal context (Low and Abrahamson 1997), extant research does not fully acknowledge the power-laden nature of the taken-for-granted notions of what constitutes desirable entrepreneurial practices (Bruni et al., 2004). We recognize entrepreneurship as a set of practices intrinsically intertwined with the very fabric of contemporary society (Nicholson and Anderson 2005), and examine one specific aspect of the entrepreneurial process: the attainment of legitimacy by entrepreneurs entering a business field. Drawing from Bourdieu’s theory of practice (Bourdieu, 1977; 1990), we conceive of the legitimacy attributed to entrepreneurs as consisting of elements that capture both stability and change, i.e., an expectation to “fit in” (institutional legitimacy) as well as to “stand out” (innovative legitimacy). We examine antecedents and outcomes of these seemingly contradictory facets of legitimacy.