Personalized outfit recommendation remains a complex challenge, demanding both fashion compatibility understanding and trend awareness. This paper presents a novel framework that harnesses the expressive power of large language models (LLMs) for this task, mitigating their "black box" and static nature through fine-tuning and direct feedback integration. We bridge the item visual-textual gap in items descriptions by employing image captioning with a Multimodal Large Language Model (MLLM). This enables the LLM to extract style and color characteristics from human-curated fashion images, forming the basis for personalized recommendations. The LLM is efficiently fine-tuned on the open-source Polyvore dataset of curated fashion images, optimizing its ability to recommend stylish outfits. A direct preference mechanism using negative examples is employed to enhance the LLM's decision-making process. This creates a self-enhancing AI feedback loop that continuously refines recommendations in line with seasonal fashion trends. Our framework is evaluated on the Polyvore dataset, demonstrating its effectiveness in two key tasks: fill-in-the-blank, and complementary item retrieval. These evaluations underline the framework's ability to generate stylish, trend-aligned outfit suggestions, continuously improving through direct feedback. The evaluation results demonstrated that our proposed framework significantly outperforms the base LLM, creating more cohesive outfits. The improved performance in these tasks underscores the proposed framework's potential to enhance the shopping experience with accurate suggestions, proving its effectiveness over the vanilla LLM based outfit generation.