A refined a priori error analysis of the conforming and non-conforming Virtual Element Method (VEM) is developed for approximating a model Poisson problem. A set of new geometric assumptions is proposed on shape regularity of polygonal meshes. A new universal error equation for the VEM is derived for any choice of stabilization, and a new stabilization using broken half-seminorm is introduced to incorporate short edges naturally into the a priori error analysis on isotropic elements. The error analysis is then extended to a special class of anisotropic elements with high aspect ratio originating from a body-fitted mesh generator, which uses straight lines to cut a shape regular background mesh. Lastly, some commonly used tools for triangular elements are revisited for polygonal elements to give an in-depth view of these estimates' dependence on shapes.