In this work, the mechanics of cone penetration during CPTu tests in Osaka clay, a natural structured silty clay, was investigated with the Particle Finite Element Method (PFEM). To describe the behavior of the soil, the FD_MILAN model, recently proposed by the Authors, was adopted. The model, based on the multiplicative decomposition of the deformation gradient, incorporates a scalar internal variable, the bond strength Pt, to quantify the effects of structure. The macroscopic description of mechanical destructuration effects is provided by the hardening law of Pt, according to which the bond strength decreases monotonically with accumulated plastic deformations. The brittle behavior resulting from the softening process associated to destructuration make the soil quite susceptible to the spontaneous development of strain localization in the form of shear bands. In order to deal with strain localization phenomena, the model is equipped with a non-local version of the hardening laws, incorporating a material constant – the characteristic length ℓc – which provides the material with an internal length scale. The objective of this work was to get some insight on the effects of the characteristic length and of the initial degree of structure on: the kinematics of the soil deformation around the advancing cone tip; the evolution of soil structure with accumulated plastic deformations; the excess pore pressure field generated in the soil as a result of the hydro-mechanical coupling between the solid skeleton and the pore water, and the net cone resistance measured at the base of the cone. The results of the PFEM simulations show that the deformations around the piezocone are strongly affected by the characteristic length. For heavily structured soils, when ℓc is relatively small with respect to cone radius, the accumulated plastic deviatoric deformation field is characterized by clearly visible shear bands while, as ℓc increases, the detection of localized deformation regions becomes more difficult, if not impossible. This depends on the fact that, for large values of ℓc, the shear band width may be of comparable size to the cone radius. In all cases, the soil around the advancing piezocone is subjected to a very strong destructuration process, which leads to the complete loss of bond strength in a large region around the cone tip and shaft. As a consequence, the use of conventional Nc values from the literature in the interpretation of the CPTu test performed in heavily structured soils could provide undrained strength values closer to the ultimate undrained shear strength. At the same time, the use of empirical correlation to estimate the yield stress in oedometric conditions would lead to a significant underestimation of the overconsolidation ratio.