Using the case of outdoor shell jackets, this research studies obsolescence and potential lifespan extension by re-examining how product functionality, objectively and subjectively, develops over the course of product lifespans. In particular, the study focuses on second-hand stores for outdoor products. Functionality is indicated by user perceptions, visual assessments, laboratory measurements and price data, collected at first use, second-hand resale and end-of-life. Perceived functionality and price decline more rapidly (5–6 % per year) than assessed and measured functionality (around 3 % per year). This could be explained by properties related to appearance, which are not assessed nor measured but influence user perceptions and price. Discontentment regarding such properties appears more relevant for obsolescence than inadequate performance, suggesting the potential for design for attachment and timeless design. The relative stability of measured functionality over time suggests that a barrier for second-hand sales, concern about performance, could be ameliorated by a potential functionality-label.