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In this paper, I empirically interrogate the concept of ‘cultural intermediaries’ through an analysis of the status of online fashion organizations as legitimacy brokers in the institutional field of fashion. Using a critical distinction between the concepts of brokerage, curation, and intermediation overlooked in cultural studies, the sociology of culture and the organizational literature, I argue that the concept of ‘intermediation’ alone can no longer sustain and represent emergent discursive practices accounted for in the fashion industry. By using examples from my 2-year ethnography and interview data with Italian and US-based online fashion retail organizations and fashion brands in New York and Milan, I argue that by exploiting the division of aesthetic labor that exists between retailers and publishers online, digital fashion organizations engage in two constituent practices of entrepreneurial play that mediate aspirations for learning and claims for cultural legitimacy to established fashion brands. I propose to revisit the status of cultural players positioned between brands and consumers, opening up questions about the process of gaining legitimacy in established industries, and the relationship between culture and knowledge, economy and culture.