Outfittery is an online personalized styling service targeted at men. We have hundreds of stylists who create thousands of bespoke outfits for our customers every day. A critical challenge faced by our stylists when creating these outfits is selecting an appropriate item of clothing that makes sense in the context of the outfit being created, otherwise known as style fit. Another significant challenge is knowing if the item is relevant to the customer based on their tastes, physical attributes and price sensitivity. At Outfittery we leverage machine learning extensively and combine it with human domain expertise to tackle these challenges. We do this by surfacing relevant items of clothing during the outfit building process based on what our stylist is doing and what the preferences of our customer are. In this paper we describe one way in which we help our stylists to tackle style fit for a particular item of clothing and its relevance to an outfit. A thorough qualitative and quantitative evaluation highlights the method's ability to recommend fashion items by style fit.
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