Buckles for inflatable personal restraint systems and associated systems and methods. In one embodiment, a buckle assembly can include a body and a latching mechanism carried by the body. The latching mechanism is configured to engage a corresponding tongue portion when the tongue is inserted into a front portion of the body. The buckle assembly also includes a cover operably coupled to the body and configured to pivotably move about an axis between a first position in which the latching mechanism engages the tongue and a second position in which the latching mechanism disengages the tongue. The buckle assembly further includes one or more counterweight components carried by the body and positioned such that the buckle assembly has a center of gravity (a) between the front portion of the body and a vertical plane extending through the axis, and (b) below a horizontal plane extending through the axis.