Um… you do know that was after his career in the Obsidian Order, right? He was kinda exiled… I mean, I’d love to see a Garak-focused prequel series that also runs until the end of the Dominion War (because you never really ever leave the Obsidian Order), telling some DS9 plot points from his perspective… but I don’t think the whole tailoring thing was ever more than part of a cover he learned as a spy that he turned into a pseudo-career during exile.