Many complex networks erase parts of their geometry as they develop, so that their evolution is difficult to quantify and trace. Here we introduce entropy measures for quantifying the complexity of street orientations and length variations within planar networks and apply them to the street networks of 41 British cities, whose geometric evolution over centuries can be explored. The results show that the street networks of the old central parts of the cities have lower orientation/length entropies - the streets are more tightly ordered and form denser networks - than the outer and more recent parts. Entropy and street length increase, because of spreading, with distance from the network centre. Tracing the 400-year evolution of one network indicates growth through densification (streets are added within the existing network) and expansion (streets are added at the margin of the network) and a gradual increase in entropy over time.