The workwear market is growing, but ways to reduce its environmental impacts remain unexplored. We investigate product designs and business models that prolong the lifetime of construction workwear in the Swedish context. Lifecycle Assessments, user interviews, focus groups, user trials, user survey, provider interviews, and participatory workshops were combined to (i) understand the status quo of the workwear market, (ii) develop six product designs and business models for circular workwear, and (iii) assess and trial them in practice. This was done from a user, customer, provider, and environmental perspective. All product design and business model innovations (design for durability, design for repair, design for washing, repair-as-a-service, washing-and-repair-as-a-service, workwear-as-a-service) are expected to improve environmental performance, however, some approaches proved ineffective due to lacking user acceptance or economic viability. Insights into the workwear industry's status quo and entirely novel knowledge on workwear consumption, challenges, and opportunities for an extended workwear lifetime in a circular economy are reported.