this man deserves an award.
My personal headcanon for Garak’s watermelon-suite is that it was hip and he looked smoking hot in it about 20 years ago, and when goes about making advances towards some cute little doctors he wears what has proved to be effective ages ago.
Then he realized like about year later that he’s trying to dress like slim Obsidian Order operative back in the year one and two and not like a sophisticated older gentleman. Then he has a mid-life crisis, which resolves itself by getting a more complimentary wardrobe. Not boring though! As fab as before, just a touch more elegant for a man of his posture.

shiny-good-rock
sagansense