A method, computer program product, and computing system are provided for identifying an advertising opportunity on a first website in response to a user accessing the first website. Information associated with the user accessing the first website may be received. One or more digital advertisements of one or more fashion products from the second website may be provided for rendering on the first website based upon, at least in part, one or more fashion-ability scores representative of the one or more fashion products on the second website and the information associated with the user accessing the first website.