First introduced in 1888 by George Key for the workers building the Manchester Ship Canal, the donkey jacket was designed as protection against the harshest elements. Its name is thought to reference the "donkey engines" used on construction sites, but its reputation quickly spread beyond the docks and railways. Over time, it became a symbol of resilience and rebellion, embraced by navvies, trade unionists, and eventually the rockabillies, Teddy Boys, and skinheads of the 20th century.

Originally constructed from thick Melton wool with leather or PVC panels for added durability, the donkey jacket was as practical as it was iconic. It represented the grit of British labourers and the understated cool of those who rejected mainstream trends.