The ‘outstanding universal value’ of the grachtengordel is specifically recognized as a seventeenth/century monument of urban design, a well preserved ‘unique and complex urban landscape’ (Unesco Nomination, 2009: 106-107). Although its four centuries of history are acknowledged, and ‘the series of almost 4,000 listed buildings – houses and warehouses, churches, charitable institutions and almshouses – and hundreds of historic bridges within the ‘property’ show great architectural diversity’ (Idem: 94), the protection of the urban composition is accentuated. The Dutch Monuments Act and the Amsterdam municipal bye-law, as well as additional protective measures and regulations are in place to protect the grachtengordel and its buildings. To safeguard the revered ‘spirit’ of the grachtengordel, understanding what determines its architecture, the character of its buildings and their transformation over time is crucial to steer future developments. This article focuses on the varied architecture of the individual buildings that together make up the gordel’s colourful palette of streetscapes as it exists today. It presents a re-reading of four centuries of designing, building and changing to uncover, out of its multi-layered evolution and multiple architectural idiosyncrasies, the essence of a unique monument. It is argued that this essence provides the ideal preconditions for future development and architectural projects, whilst respecting its monumental status.