An on-chip structure consisting of a round-cornered square-shaped (RCSS) resonator as an optical filter is studied via optical experiments, analytical modeling, and numerical techniques. A general coupling model is shown to accurately represent the entire spectral response; the model also provides an understanding of the influence of geometrical and coupling parameters on the resonance characteristics of the RCSS microresonators. The selection of an optimum radius of curvature for rounding off the sharp corners of square microresonators can provide higher quality factors than that of conventional circular resonators. The rotation of the RCSS at the central corner coupling point is also shown to improve the quality factor and remove the minimal phase mismatch requirement and dependency on interaction length. The model results are validated with an electromagnetic finite domain analysis (EMFD) and optical experiments, for which an RCSS on a silicon-on-insulator platform is fabricated. It is shown that the optical performance characteristics (quality factor, transmission ratio, and extinction ratio) of the microresonators are very sensitive to the coupling parameters and must be carefully considered in addition to geometrical length, rotation, and curvature effects. Due to the change in coupling introduced by rotation, the quality factor of the round-cornered square-shaped microresonator can be significantly larger than a circular ring with the same size, thereby establishing RCSS as a competitive alternative to circular microresonators.