Sewing machine and sewing method

A sewing machine is disclosed. The sewing machine includes a holding member configured to be movable while holding a workpiece within a predetermined plane including a sewing position immediately below a needle, an actuator configured to move the holding member, an imaging device configured to be capable of capturing the workpiece, a sewing data acquisition unit configured to acquire sewing data including a sewing order to be referred to in sewing processing, and an imaging position setting unit configured to output a control signal to the actuator so that a plurality of feature patterns of the workpiece are sequentially disposed in an imaging region of the imaging device based upon the sewing data.