Larkin’s famous ‘Englishness’ faced the challenge of coping with the changes and compromises England as a place was going through in the so-called ‘swinging Sixties’. The boom of consumerism and commercial media, the sexual revolution resulting from the invention of contraceptives and birth control devices began to unsettle the age-old values. Society became more permissive. The rise of advertising, television and broadcast media, records, gramophone, fashionable clothing has been a kind of shock to the older generation. Homosexuality was legalised. As a university librarian Larkin also came across new developments in the realm of education. There is a common tendency among the critics of 1990s to locate Larkin’s sense of being out of place in the rapidly changing physical as well as the cultural geography of England of the time. Through a detailed discussion of the poems of The Whitsun Weddings (1964) and High Windows (1974) this chapter aims to show that although Larkin was occasionally critical to the changes and compromises of the time, his “Englishness” has nothing to do with a sense of threatened nationalism as his works has continued to reflect upon a sense of placelessness from the very beginning.