Techniques are disclosed for generating image recommendations to facilitate the sale of a product. An example methodology includes identifying a product category associated with an image of the product provided by the seller, and a product sub-category associated with the product image. The method further includes retrieving one or more images of for-sale items. The retrieval is based on a search of for-sale listings using the identified product category and the identified product sub-category. The method further includes clustering the retrieved images of for-sale items into groups, each group associated with a perspective viewpoint of the for-sale item. The method further includes providing a selected image from each group as an image recommendation. The selection is based on a value score associated with each of the images of the for-sale items. A graphical status indicating completeness of the seller's image set is updated in response to recommended images being adopted.