System (10) for automatically packaging items varying in size and number for shipment, comprising a unit (32) for acquiring size information of one or more item(s) to be packaged, an inner packaging material feeding unit (24) for feeding an inner packaging material, an outer packaging material feeding unit (26) for feeding an outer packaging material, a first wrapping station (16) for wrapping said inner packaging material around one or more item(s) to be packaged to create an inner packing surrounding the item(s) in a first direction and a second wrapping station (18) for wrapping said outer packaging material around said inner packing to create an outer packing surrounding the inner packing in a second direction, said second direction being substantially perpendicular to said first direction, wherein the first and the second wrapping stations are adapted to form said inner packing and said outer packing such that the inner and the outer packing form a combined package enclosing the packaged item(s) from all sides.