An underwear with shirt tucking apparatus includes a lower undergarment, a second waist band, a plurality of attachments, and a plurality of gaps. The second waist band is circumferentially positioned around a first waist band of the lower undergarment and connected to the first waist band by the attachments. The attachments include a sagittal attachment, a first lateral attachment, and a second lateral attachment as the sagittal attachment is positioned along a sagittal plane of the lower undergarment and adjacent to a front section of the lower undergarment. The first lateral attachment and the second lateral attachment are positioned adjacent to a rear section of the lower undergarment. Resultantly, the sagittal attachment, the first lateral attachment, and the second lateral attachment are equally spaced around a circumference of the first waist band, delineating the plurality of gaps for a shirt to be tucked.