Custom tailors working in the informal sector in Nairobi, Kenya, mainly acquire technical skills through undertaking traditional apprenticeships (TAs). However, most of these tailors are semi-skilled, produce low-quality products and are often poorer than their formally trained counterparts. This qualitative case study explores the aspects of technical skills and knowledge which tailoring apprentices develop, and the factors which influence these outcomes. The findings show that apprentices do acquire basic technical "skills" for immediate application to ongoing tailoring activities (such as how to take body measurements, draft patterns, and cut, sew and finish constructed garments). However, apprentices do not acquire the technical "knowledge" that underpins the trade. Most master tailors who have completed TAs lack technical knowledge and have no access to technical skills upgrading. This perpetuates the cycle of basic and limited technical skills transfer to apprentices, poor performance and poverty among tailors. Both apprentices and master tailors expressed concern over knowledge limitations in TAs and a need to access further training to improve skills and acquire knowledge of the trade. The authors of this article argue that, technically and pedagogically, skilled master tailors are critical to improving training quality. Complementary training in theoretical knowledge is also important in improving apprentices' technical skills and understanding of the trade. Inclusion of TAs in government policy may help ensure sustainable improvement of skills.