'hipness' originates from English, specifically the slang word 'hip', where 'hip' meant 'in the know; fashionable'.

'hip' developed in early 20th-century American English (related to earlier slang 'hep'); 'hipness' was formed later by adding the nominalizing suffix '-ness' to create the noun meaning 'the state of being hip'.

Initially, 'hip' meant being 'informed' or 'aware' (especially of trends); over time this shifted to emphasize fashionable style and coolness, which is the sense behind 'hipness'.