This special issue collects selected contributions (excluding general lectures) of a Symposium on "Micro to MACRO Mathematical Modelling in Soil Mechanics", which took place at the University of Reggio Calabria, Italy, from May 29th to June 1st, 2018. The Symposium provided an opportunity to enhance the scientific debate on the construction of mathematical models for the description of the physical behaviour of soils, as well as on the suggestions provided by the micro-mechanical observation of the matter. The focus was on the comparison between the appropriateness of models and the need of mathematics to obtain rigorous results, which involves know-how from applied mathematical physics, geotechnical engineering and mechanics of solids.