For my bachelor thesis, I developed Lettermatch, a monogram ideation web app designed to bridge the gap between static inspiration and technical execution. I recognized that traditional mood boarding often fails in typography because the specific geometry of a letter—like the rigid angles of an ‚E‘ versus the curves of an ‚O’—dictates which concepts are actually viable. To solve this, I designed a search interface driven by letterform pattern recognition, allowing designers to instantly find concepts compatible with their specific character pairs. By categorizing typographic ideas through their structural DNA, the tool automates the ‚compatibility check‘ that usually slows down early-stage design. This project focused on transforming a manual, high-friction creative process into a high-speed, logical workflow. The result is a system that empowers designers to move from initial research to matching concepts with professional precision.