This paper deals with the buckling and postbuckling responses and the progressive failure of square symmetric laminates with rectangular cutouts under uniaxial compression. A detailed investigation is made to show the effects of cutout size and cutout aspect ratio on prebuckling 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 load, failure loads, failure modes and maximum transverse deflection for a $(+45/-45/0/90)_{2s}$ laminate with and without cutout have also been presented. It is concluded that square laminates with small square cutouts have more postbuckling strength than without cutout, irrespective of boundary conditions.