An information processing system includes: a vehicle configured to capture an image of clothing and accessories of a user when the user gets in the vehicle to generate a clothing and accessories image; and a server configured to communicate with the vehicle and a terminal device of the user. The server is configured to: train a supervised learning model by using at least one of schedule information of the user and weather information as input data and clothing and accessories information as training data; estimate clothing and accessories according to at least one of schedule information of the user and weather information for the next time the user gets in the vehicle by using the trained supervised learning model; and send clothing and accessories recommendation information indicating the estimated clothing and accessories to the terminal device of the user.