A native of Tillingham in Essex, Oskyn became a freeman of Colchester in 1402-3.
Oskyn played a full role in the public affairs of his borough. A member of the local guild of St. Helen,
Oskyn died on 4 Oct. 1445, a few weeks after he was elected bailiff for a fourth time. John Beche* was elected in his stead shortly afterwards. His wife survived him and, in January 1447, she again stood charged with the offence of forestalling goods. It is not clear if the couple had any children, although it is possible that Roger Oskyn, who had delivered a consignment of cheese to another merchant on the MP’s behalf in 1423, was their son.
