This thesis considers different aspects of the utilization of contour information and syntactic and semantic image segmentation for object registration, modeling and retrieval in the context of content-based indexing and retrieval in large collections of images. Target applications include retrieval in collections of closed silhouettes, holistic w ord recognition in handwritten historical manuscripts and shape registration. Also, the thesis explores the feasibility of contour-based syntactic features for improving the correspondence of the output of bottom-up segmentation to semantic objects present in the scene and discusses the feasibility of different strategies for image analysis utilizing contour information, e.g. segmentation driven by visual features versus segmentation driven by shape models or semi-automatic in selected application scenarios. There are three contributions in this thesis. The first contribution considers structure analysis based on the shape and spatial configuration of image regions (socalled syntactic visual features) and their utilization for automatic image segmentation. The second contribution is the study of novel shape features, matching algorithms and similarity measures. Various applications of the proposed solutions are presented throughout the thesis providing the basis for the third contribution which is a discussion of the feasibility of different recognition strategies utilizing contour information. In each case, the performance and generality of the proposed approach has been analyzed based on extensive rigorous experimentation using as large as possible test collections.