According to one aspect of an exemplary embodiment of the disclosure, a mammography imaging system or device includes a brassiere including one or more inflation chambers to assist in automatically positioning the breast. The brassiere includes cup in which the breast is positioned that includes a radiolucent cushion material along with the chambers and one or more inflatable chambers to compress/push the breast forward to position the breast within the cup as desired. In addition, the brassiere includes a vacuum system secured to the front part of the cup to pull the tip or nipple portion of the breast forward with vacuum-based suction technique. With the initial compression of the breast within the cup, the compression paddle of the imaging system can then be employed to apply any necessary additional force across the breast to achieve the required breast position and thickness for the selected image view, with the cushion material limiting any discomfort from the compression.