A sewing system includes a cutting device and a sewing machine. The cutting device acquires the cutting data and send the cutting data via at least one of the network line or at least one of the wireless communication by the cutter communication portion. The sewing machine receives the cutting data sent by the cutting device via at least one of the network line or at least one of the wireless communication. The sewing machine generates the embroidery data, based on the cutting data received by the sewing machine. The sewing machine sews on the object to be sewn, based on the generated embroidery data.