Introduction: Bones, as whole skeletal structures, adapt to mechanical stresses they customarily experience. Because the present, mechanized lifestyle apparently deprives our skeletons of vigorous, habitual physical exertion, we studied whether the proximal femur phenotype has evolved vulnerable to fragility fractures by time. Materials and Methods: Proximal femur macroanatomy of 118 medieval and 67 contemporary adults, 84 contemporary elderly, and 48 contemporary hip fracture cases was evaluated. Using direct measurements of external bone dimensions and geometric properties, we estimated the fall-induced stress as an index of hip fragility. Results: Within similar to 1000 years, the femoral axis length has become substantially longer (analysis of covariance, body height adjusted, p < 0.001), whereas the neck circumference has not increased. The macroanatomy was found similar between the contemporary adult and elderly groups. In hip fracture cases, however, the femoral axis length was further lengthened (p < 0.001), but the circumference was somewhat smaller (p = 0.001). Consequently, the estimated fall-induced stress can be similar to 1.5-fold today compared with the medieval times (p < 0.001), and the secular trend seemed to be worse in women (sex-time interaction, p = 0.001). Conclusions: The modern, relatively slender phenotype of the proximal femur alone seems to increase the fall-induced stress considerably, and when this phenotype coincides the osteoporotic, internally deteriorated femoral neck structure, fracture risk is imminent. This mechanically compromised external phenotype underscores the importance of timely strengthening of the skeleton and its regular maintenance throughout life.