The mechanical quality of trabecular bone depends on both its stiffness and its strength characteristics, which can be predicted indirectly by the combination of bone volume fraction and architectural anisotropy. To analyze the directional anisotropy of the trabecular bone, we applied the fractal geometry technique to plain radiographs. The anisotropy of the bone was quantified from an ellipse, based on the directional fractal dimensions (FD), by the principal axes of inertia. The anisotropies based on the FD were compared with those determined using the common method of mean intercept length (MIL). The directional FD gave the fractal information obtained from a projection along the MIL orientation. For this reason, the spatial variations associated with the bone length in any direction were manifested in a related frequency band of the power spectrum determined along the direction. The directional FD and MIL plots were highly correlated, although they originated from quite different geometries. Of the angle, premolar, and incisor regions of the human mandible, the anisotropies calculated using both FD and MIL showed the highest correlation in the trabecular bone of the angle region. The method using directional FDs as determined by the principal axis of inertia measures the anisotropy directly, using two-dimensional plain radiographs. This kind of method will be a useful to provide better estimates of bone quality in vivo compared with the density measurements alone, especially for the indirect diagnosis of jawbone quality in dental clinics.