This paper reports and studies three fashion logistics optimization-related problems, including fashion distribution, transshipment, and sustainable logistics management. Fashion products are popular in the context of e-commerce and business innovation. The responsiveness of product searching, purchasing, experiencing, and returning or disposal is critically important. In this paper, considering the consumer experience during the distribution service, the try-on service is introduced and examined, where the effects of try-on services on return ratios, loyalty, and logistics cost are analyzed based on experiments. Then, to share fashion products among retailers of a brand, transshipment is critical and this paper presents an analytical model for investigating transshipment. By transshipment, fashion products can be efficiently transported from, e.g., the selling-well "good business" retailers to the "poor business" retailers. Next, considering the short life cycles of fashion products, a sustainable supply chain model is devised by using rental services in the loop. The operations problems and systematic mechanisms are then explored based on the model. Finally, the challenges and opportunities of using advanced technologies (e.g., Internet of Things and big data) are discussed. The proposed models in this paper provide important references for fashion industrialists as well as academics on fashion logistics and supply chain management.