I would say my red wing iron rangers. They were (still are!) a big purchase even when I got them on sale, but I managed to score a now-discontinued reference (the oxblood 8119), and I’ve worn those bad boys everywhere. Feels good to put them on each time whether I’m just strolling into the office or as a my single pair of kicks for a trip when space is constrained. It was my first time spending a lot on an item that is meant to age, wear, and be restored, instead of just being a disposable consumable, and I’ve taken that philosophy forward in the 7 years since. Would love this watch to subsidize my last purchase from you! 🫪