Previous literature in person-product attachment has identified factors in long-term relationships responsible for the strengthening of bonds between users and products, stimulating longevity in use. Interested in further understanding the matter in the realm of fashion, this study investigates how relationships between individuals and the clothes they wear evolve over time. It identifies motivators behind the increase and decrease in the overall quality of wearer-worn relationships in regards to four dimensions: comfort, frequency of use, visuality and versatility. In order to achieve this aim, an adaptation of the UX curve method is used. The method was employed with a group of ten participants, wearers of specific clothing production, namely experimental-fashion, in contrast with commercial-fashion pieces. The study findings contribute to the literature on person-product attachment and highlight ‘learning to wear’ as an engaging experience encouraging stronger relations with clothes. In the discussion, the article proposes future endeavours to understand wearing practices aiming at more engaging designs.