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Against the backdrop of the widespread individualization of the creative workforce, the last decade has witnessed a proliferation of socially mediated forms of production that reside in the traditionally feminine domains of fashion, beauty, domesticity, and craft. This paper explores how participants in one of these genres—fashion blogging—represent themselves in their textual and visual content. Bringing a systematic sample of top-ranked blogger narratives and Instagram images together with data from in-depth interviews, we show how bloggers depict an idealized version of “having it all” through three interrelated tropes: passionate work, the “glam life,” and carefully curated social sharing. These tropes articulate a form of “entrepreneurial femininity” that draws on post-feminist sensibilities and the contemporary logic of self-branding. Yet, we argue that these depictions obscure the labor, discipline, and capital necessary to emulate these standards.