While many shields depicted on Greek pottery bear a single central image, examples exist in several areas that suggest that more complex designs were conceivable to the Greeks. In this work, we present three shields painted for use in the Society for Creative Anachronism that embrace the “creative” artistic element within our society, but that also are deeply inspired by the archeological record. It was not our intent to produce perfect reconstructions of Ancient Greek shields. Rather, we wished to adorn shields chosen by the bearers for their fitness (weight, shape, size, etc.) with an aesthetic that an Ancient Greek would recognize, while also allowing for some artistic expression on the part of the painter.