With 2020’s deluxe release of Prince’s magnum opus Sign o’ the Times, fans were reintroduced to the era’s distinct sartorial blueprint of peach and black, denim and fringe. Unexpectedly, the Sign o’ the Times signature look is largely regarded as the oversized customized denim jacket worn by Prince throughout the concert film and live performances. Not just your typical denim jacket, the garment is adorned with decorative safety pins, buttons, graphic appliqués, fringe and various glittering embellishments. Like Purple Rain’s studded trench coat, the denim jacket is now forever affiliated with Sign o’ the Times, active throughout our shared popular culture conscious. Within the expansive wardrobe of the musician, the denim jacket remains a unique cultural artefact, not only for the unexpected utilitarian fabric choice but also for the garment’s coded signifiers of the counterculture, liberation and community. An object study of the denim jacket will examine the strategies employed in Prince’s shared visual language, transmedia storytelling and fan-generated clothing. Through an interdisciplinary investigation informed by theoretical work in fashion, media, film and cultural studies, the article seeks to examine how Prince’s bespoke denim jacket both fuels consumption and facilitates placemaking and community building both in physical and digital contexts still to this day.