Assisted clustering systems and methods are described herein that provide a user interface by which a user can easily create clusters and selectively associate data items with such clusters. Information regarding data item-cluster associations made by the user is processed by a recommendation engine to learn a clustering model. The clustering model is then be used to generate recommendations for the user regarding which unassociated data items should be associated with which clusters. In certain embodiments, after the user has determined that the clustering model is performing at a satisfactory level based on the quality of the recommendations, the user can cause the system to automatically cluster a large quantity of remaining unassociated data items. In accordance with further embodiments, a user can specify arbitrary data item types for clustering as well as features of such data types that should be considered in generating the clustering model.