I tend to keep my collection limited at any one time, so only a couple stand out:
Seiko Shogun (will get another if I ever sell my Pelagos)
Seiko SBBN015 Tuna - Still don't remember why I sold it. Probably thickness and that clasp. Don't like the current Tuna's nearly as much.
Blue Aquaracer - not a DWC favorite, but I bought it mint for $700, and should have kept it for beater duties for the price. Super comfortable and kept great time.
Stowa Seatime - I loved that shade of blue.......
It is the sub $1k watches that I regret selling as I could probably live with a few minor issues at that pricepoint. More expensive watches for me need to check all boxes, and if they have an uncomfortable clasp, or are too thick, etc.... they must go.