Despite the recent proliferation of articles on entrepreneurial identity in the last decade, little consideration has been given to the semiotics and aesthetics of how such identity formation is operationalised via the adoption of artefacts of success and sartorial signifiers of such success to construct, fashion and influence such identities. Using semiotic analysis techniques this article explores the deliberate fashioning of gendered elite entrepreneurial identities in the blogs of an American entrepreneur and influencer Jana Arnold. Visual data was collected and analysed to illustrate the processes involved. The findings indicate that the possession of branded clothing and artefacts, combined with their physical appearance can lead to the formation of a distinctive ‘aesthetic capital’ which confers a visual legitimacy which can be commodified as a commercialised identity. The findings also suggest that the juxtaposition of selective dress, props and settings combine to create a form of branded, elitist expressiveness conveyed via the presentation of designer fashion, branded artefacts and high value marques and products. Collectively these can coalesce to form an authenticated entrepreneurial identity for those entrepreneurs who can afford to buy and maintain the monetised identity.