We propose a flexible person generation framework called Dressing in Order (DiOr), which supports 2D pose transfer, virtual try-on, and several fashion editing tasks. The key to DiOr is a novel recurrent generation pipeline to sequentially put garments on a person, so that trying on the same garments in different orders will result in different looks. Our system can produce dressing effects not achievable by existing work, including different interactions of garments (e.g., wearing a top tucked into the bottom or over it), as well as layering of multiple garments of the same type (e.g., jacket over shirt over t-shirt). DiOr explicitly encodes the shape and texture of each garment, enabling these elements to be edited separately. Extensive evaluations show that DiOr outperforms other recent methods like ADGAN  in terms of output quality, and handles a wide range of editing functions for which there is no direct supervision.