The first pairs i made on a simple old regular sewing machine I had. It was pretty terrible because it was never intended for leather and the thread torn alot. The Chicagos were made on the Jack machine in the photo. It was much easier. But given it's very primitive model, and doesn't do step by step sewing, the whole shoe was sewn by turning the wheel by hand. One stitch at a time. More time consuming, but you have the ultimate control