Compositing aware digital image search techniques and systems are described that leverage machine learning. In one example, a compositing aware image search system employs a two-stream convolutional neural network (CNN) to jointly learn feature embeddings from foreground digital images that capture a foreground object and background digital images that capture a background scene. In order to train models of the convolutional neural networks, triplets of training digital images are used. Each triplet may include a positive foreground digital image and a positive background digital image taken from the same digital image. The triplet also contains a negative foreground or background digital image that is dissimilar to the positive foreground or background digital image that is also included as part of the triplet.