This article analyses the organisational and individual drivers and barriers to the implementation of circular business models (CBM) by incumbents and start-ups in the workwear industry. It is based on a qualitative study of 15 organisations in the Swedish workwear industry. Most incumbents are found to have either long-life models with hybrid elements, such as repair, or access models, while circular start-ups have a larger variety of CBMs, although the most common is gap exploiter. Internal organisational barriers mostly differ between the two groups; however, external organisational barriers are more significant and common, such as the low price of new workwear, a lack of demand and a lack of supporting policies, for example, public procurement. Several organisational drivers are identified, such as opportunities to deliver customer value, textile and digital innovations and environmental concerns. Drivers and barriers are influenced by both type of CBM and type of company. Individual drivers and barriers, which are often overlooked in literature, are found to be important to CBM implementation.