The “shoeboxing” algorithm is a simplification approach capable of converting a building of any shape into a representative shoebox, with the aim of speeding-up Urban Building Energy Modeling simulations. The procedure works towards accurately predicting both annual energy needs and hourly thermal loads, going beyond the preliminary assessment of buildings' thermal performance at city-scale. Furthermore, the simplification has been particularly developed to work with buildings of complex geometry considering adjacencies and obstructions. After a first validation performed for stand-alone buildings, in this paper, the capabilities of the algorithm are evaluated at district-level on fictional parametrically generated layouts and in different climatic conditions. As a whole, the shoeboxing algorithm properly predicted both heating and cooling needs at building-level in all the considered climatic conditions, yielding annual differences within ±10% and ± 20%, respectively for cooling and heating. Moreover, both annual and hourly deviations showed to be similar in the different climates considered, suggesting that the simplification can be reliably employed worldwide. Finally, the thermal simulation time has been reduced up to 36 times.