Detailed shape evolution during particle crushing was investigated using dyed gypsum particles. The particle shape information was measured from photographs with two orthogonal orientations and the Weibull function was introduced to quantify the statistical distribution of particle shapes. Then, the shape characteristics of particles under one-dimensional compression were investigated. It is found that child particles that have more size differences with parent particles are more rough, less spherical, more elongated, and flatter, with wider distribution range of shape factors. Surviving particles become more regular compared with parent particles and the distribution ranges of their shape factors tend to narrow down, whereas the broken particles show the opposite changing trends. However, all particles within a size range consist of both the surviving particles and the broken particles so that the overall particle shapes do not show consistent changing trends.