Deep learning-based clothing style evaluation method and system are provided. According to the present invention, a deep learning-based clothing style evaluation method comprises receiving at least one image provided by a user terminal, analyzing objects included in the at least one image and extracting a plurality of fashion features related to a user using deep learning algorithm when the user exists in the object, extracting matching information between the extracted plurality of fashion features using deep learning algorithm, evaluating a clothing style of the user based on the matching information, and transmitting an evaluation result to the user terminal, wherein the fashion feature is one of the number of clothing worn by the user, type of clothing, color of clothing, style of clothing, skin tone of the user, and other information affecting fashion style, and wherein the matching information comprises essentially of matching information between the skin tone of the user and any one of the fashion features other than the skin tone.