An information processing apparatus according to an embodiment of the present technology includes a physical information acquisition unit, a gesture information acquisition unit, a determination condition setting unit, and a control unit. The physical information acquisition unit acquires physical information of a user wearing a head-mounted casing. The gesture information acquisition unit acquires gesture information regarding a gesture of the user. The determination condition setting unit sets, on the basis of the physical information, a determination condition for determining a trigger gesture that is a trigger for an operation input by the gesture of the user. The control unit determines, on the basis of the gesture information and the determination condition, whether or not the trigger gesture is performed and controls, on the basis of a result of the determination, an output corresponding to the trigger gesture.