Composed image retrieval (CIR) requires complex reasoning over heterogeneous visual and textual constraints. Existing approaches largely fall into two paradigms: unified embedding retrieval, which suffers from single-model myopia, and heuristic agentic retrieval, which is limited by suboptimal, trial-and-error orchestration. To this end, we propose OSCAR, an optimization-steered agentic planning framework for composed image retrieval. We are the first to reformulate agentic CIR from a heuristic search process into a principled trajectory optimization problem. Instead of relying on heuristic trial-and-error exploration, OSCAR employs a novel offline-online paradigm. In the offline phase, we model CIR via atomic retrieval selection and composition as a two-stage mixed-integer programming problem, mathematically deriving optimal trajectories that maximize ground-truth coverage for training samples via rigorous boolean set operations. These trajectories are then stored in a golden library to serve as in-context demonstrations for online steering of VLM planner at online inference time. Extensive experiments on three public benchmarks and a private industrial benchmark show that OSCAR consistently outperforms SOTA baselines. Notably, it achieves superior performance using only 10% of training data, demonstrating strong generalization of planning logic rather than dataset-specific memorization.

Image retrieval has traditionally been formulated as a point-wise matching problem, where each candidate image is scored in isolation. However, this atomic paradigm fails to capture the complexity of human search intent within personal photo collections, where users often seek compact visual stories bound by structural relations rather than isolated snapshots. To address this limitation, we introduce **Image Bundle Composition (IBC)**, a novel paradigm that shifts the objective from ranking individual images to dynamically composing cohesive image bundles from a massive, unstructured photo pool. Since target bundles are not predefined, IBC presents a severe combinatorial explosion challenge and demands modeling non-decomposable joint relevance. To establish this paradigm, we construct **IBCBench**, the first IBC benchmark dataset containing 109,467 images and 667 verified queries, built via a semi-automated verification pipeline. Furthermore, we propose **BundleWeaver**, an agentic framework that reformulates IBC as query-conditioned incremental hyperedge discovery. By employing a Large Language Model to adaptively search for missing relational roles and utilizing a Vision-Language Model for whole-bundle verification, BundleWeaver effectively navigates the combinatorial space. Extensive experiments demonstrate that while state-of-the-art embedding models and static decompose-and-rerank paradigms suffer from relational blindness, BundleWeaver achieves substantial performance gains, highlighting the necessity of shifting from atomic scoring to dynamic relational composition. Our dataset and code are available.