Composing fashion outfits involves deep understanding of fashion standards while incorporating creativity for choosing multiple fashion items (e.g., Jewelry, Bag, Pants, Dress). In fashion websites, popular or high-quality fashion outfits are usually designed by fashion experts and followed by large audiences. In this paper, we propose a machine learning system to compose fashion outfits automatically. The core of the proposed automatic composition system is to score fashion outfit candidates based on the appearances and meta-data. We propose to leverage outfit popularity on fashion oriented websites to supervise the scoring component. The scoring component is a multi-modal multi-instance deep learning system that evaluates instance aesthetics and set compatibility simultaneously. In order to train and evaluate the proposed composition system, we have collected a large scale fashion outfit dataset with 195K outfits and 368K fashion items from Polyvore. Although the fashion outfit scoring and composition is rather challenging, we have achieved an AUC of 85% for the scoring component, and an accuracy of 77% for a constrained composition task.