This paper deals with the buckling and postbuckling responses, and the progressive failure of square laminates of symmetric lay-up with a central rectangular cutout under in-plane shear load. A detailed investigation is made to show the effects of cutout size and cutout aspect ratio on the buckling and postbuckling responses, failure loads and failure characteristics of $(+45/-45/0/90)_{2s}$, $(+45/-45)_{4s}$ and $(0/90)_{4s}$ laminates. The 3-D Tsai-Hill criterion is used to predict the failure of a lamina while the onset of delamination is predicted by the interlaminar failure criterion. In addition, the effects of boundary conditions on buckling loads, failure loads, failure modes, and maximum transverse deflection for a $(+45/-45/0/90)_{2s}$ laminate with and without a square cutout have been presented. It is concluded that because of early onset of delamination at the net section of cutouts before first-ply failure, total strength of the laminate with very small cutouts can not be utilized.