1. A system comprising: an access module configured to: access a set of context data, the set of context data comprising a first environment image depicting a first environment; a simulation module coupled to the access module and configured to: segment the first environment image of the environment into a first plurality of segments; identify a first ground segment from the first plurality of segments; and determine at least a first placement area within the first environment image based on the first ground segment and a first set of placement cues associated with the first plurality of segments; and an imaging module configured to: superimpose a wearable item image on the first environment image to generate a first item context base image, wherein the wearable item image is placed within the first placement area, and wherein the wearable item image comprises an image of a wearable item; identify a first erosion area in the first item context base image, the first erosion area comprising at least a portion of a boundary between the first environment image and the wearable item image; and perform an image filtering process on the erosion area to generate a first context image comprising at least a portion of the wearable item image and a portion of the first environment image.