This paper proposes a method for generating and recommending fashionable outfit images based on a given image of a fashion item. The system uses image generation AI, specifically Stable Diffusion, to produce images of a person wearing the input item, leveraging inpainting techniques to complete the surrounding area. Two models were prepared: a fashionable model fine-tuned on highly rated outfit images from social media, and a normal model without fine-tuning. Both models generated multiple images featuring the input item, and object detection techniques (YOLO and CLIP) were used to identify and count frequently appearing items. Items that appeared more often in the outputs of the fashionable model were prioritized, and the corresponding images were ranked and presented as outfit recommendations. A subject experiment was conducted to evaluate the system, demonstrating that the proposed method can recommend stylish outfits and reflect query items more effectively than metadata-based recommendations.