He trained as an architect in London and returned to work in his father's firm of builders in Norwich.

At this time Skipper, along with his rival Edward Boardman dominated building in the city.

His own office in London Street, now part of the Jarrolds departmental store, has a red brick facade, with a frieze featuring scenes of architects and builders.

It is faced with a locally-made type of terracotta called Cosseyware, made at Costessey (pronounced "Cossey") near Norwich by the firm of Guntons.

His son, Edward (1918–2005) (by his 3rd wife Elizabeth Alice Charter, née Roberts), himself an important local architect, worked with him while studying architecture.