Developing a real-world recommender system, i.e. for use in large-scale online retail, poses a number of different challenges. Interestingly, only a small part of these challenges are of algorithmic nature, such as how to select the most accurate model for a given use case. Instead, most technical problems usually arise from operational constraints, such as: adaptation to novel use cases; cost and complexity of system maintenance; capability of reusing preexisting signal and integrating heterogeneous data sources. In this paper, we describe the system we developed in order to address those constraints at Zalando, which is one of the most popular online fashion retailers in Europe. In particular, we explain how moving from a collaborative filtering approach to a learning-to-rank model helped us to effectively tackle the challenges mentioned above, while improving at the same time the quality of our recommendations. A fairly detailed description of our software architecture is provided, along with an overview of the algorithmic approach. On the other hand, we present some of the offine and online experiments that we ran in order to validate our models.