Kmart
·For me (mid-20's) it makes a hell of a lot more sense value-wise to pickup a handful of really excellent vintage dress watches than to drop 3,4,5k on an SMP/Pelagos/Submariner. In the last three months I've gotten an 18k Flagship 30L, a 14k Flagship 285, a C-case Connie, and a Grand Seiko 5646-7010. All were between $500 and $850, in great condition and have top notch, in-house movements. I'm also not going to see one on every third wrist, which makes me appreciate them even more.
That's definitely a good strategy and I wish that I could go that route. Those are all objectively great watches, but I find that they just don't speak to me the same way that classic tool watches do. I've owned a few (including a practically NOS Seamaster and a Zenith Pilot) and while beautiful, they've all ended up sold quite quickly... which is unfortunate because vintage tool watches are the most 🤬 expensive things out there due to the double whammy of their rarity in good condition (caused by the fact that a lot of them were beat to hell) and their desirability because of the history behind a lot of them.