This case study examines the role that Tall Poppy Syndrome (TPS) plays within the New Zealand jewellery industry. One company's attempt to subvert tradition and encourage personalization of milestone jewellery such as engagement rings and wedding rings has led to insights about Kiwi jewellery purchasing behaviours. The mass-market jewellery industry in New Zealand is heavily invested in producing jewellery designs that have existed for upwards of 50 years. Kiwi customers are on average less adventuresome in their preference for jewellery styles, and often purchase traditional jewellery designs because they believe such designs to be stylistically safer. This paper provides a detailed case study that examines how the Auckland-based boutique jeweller K. Amani Fine Jeweller designs against convention and consistently encourages tradition-minded customers to embrace personalized jewellery styles. This is accomplished through communicating to customers the personal design aesthetic of K. Amani’s jeweller, as well as through non-standard solutions to traditional jewellery manufacturing such as Computer Aided Design (CAD), 3D rendering, and 3D printing. Likewise, dedicated face-to-face consultations and a keen understanding of customer personality types help to raise awareness of jewellery design possibilities, and provide customers with a greater sense of security in order to opt for custom or non-traditional designs. This approach consistently results in customers electing personalized touches to their jewellery designs, and encourages lifetime loyalty to K. Amani who can create custom designs, versus jewellers that only provide stock items.