A window dressing comprising: a primary layer having a lower, skin-facing surface and an upper surface, the primary layer having a first stiffness and comprising a window portion having a window formed therein and a securement portion; a primary adhesive layer covering at least a portion of the skin-facing surface of the primary layer; a support structure attached to the upper surface of the primary layer within the securement portion, the support structure comprising: a structural layer having a lower surface and an upper surface, the structural layer having a second stiffness, and an adhesive layer covering at least a portion of the lower surface of the structural layer and adhering the structural layer to the upper surface of the primary layer; a transparent layer attached to the upper surface of the primary layer and covering the primary layer, the primary layer window, and at least a portion of the structural layer, the transparent layer comprising: a transparent film having a lower surface and an upper surface, and an adhesive layer covering at least a portion of the lower surface of the transparent film and adhering a portion of the transparent layer to the top surface of the primary layer; characterized in that said second stiffness is greater than said first stiffness and in that a portion of the support structure extends beyond a periphery of the primary layer and wherein the portion of the support structure extends beyond a periphery of the transparent layer. a primary layer having a lower, skin-facing surface and an upper surface, the primary layer having a first stiffness and comprising a window portion having a window formed therein and a securement portion; a primary adhesive layer covering at least a portion of the skin-facing surface of the primary layer; a support structure attached to the upper surface of the primary layer within the securement portion, the support structure comprising: a structural layer having a lower surface and an upper surface, the structural layer having a second stiffness, and an adhesive layer covering at least a portion of the lower surface of the structural layer and adhering the structural layer to the upper surface of the primary layer; a structural layer having a lower surface and an upper surface, the structural layer having a second stiffness, and an adhesive layer covering at least a portion of the lower surface of the structural layer and adhering the structural layer to the upper surface of the primary layer; a transparent layer attached to the upper surface of the primary layer and covering the primary layer, the primary layer window, and at least a portion of the structural layer, the transparent layer comprising: a transparent film having a lower surface and an upper surface, and an adhesive layer covering at least a portion of the lower surface of the transparent film and adhering a portion of the transparent layer to the top surface of the primary layer; characterized in that said second stiffness is greater than said first stiffness and in that a portion of the support structure extends beyond a periphery of the primary layer and wherein the portion of the support structure extends beyond a periphery of the transparent layer. a transparent film having a lower surface and an upper surface, and an adhesive layer covering at least a portion of the lower surface of the transparent film and adhering a portion of the transparent layer to the top surface of the primary layer; characterized in that said second stiffness is greater than said first stiffness and in that a portion of the support structure extends beyond a periphery of the primary layer and wherein the portion of the support structure extends beyond a periphery of the transparent layer.