I'm not a watch enthusiast by any stretch (I wear a 9y/o $200 Citizen Ecodrive) but knowing some people who are, they tend to geek out over the craftsmanship that goes into automatic (mechanical) watches. A good automatic watch is one of the few things you can still buy that's mostly handmade, extremely high quality, and will last basically forever. Given that most of the things we buy these days are just Chinese shit, I can understand the idea of spending a fair amount of money for something extremely well built that you can hand down to your son and grandson some day. Now, sometimes they take this to silly lengths with the $XX,XXX and $XXX,XXX watches, but I get the point, even if I don't have the desire myself.
Really the worst type of watches are those that are in the low $1000s range that are not automatic, not handmade, and just gaudy versions of a $40 Fossil and "valuable" solely because they're expensive. A real high-quality mechanical watch will also not depreciate too much, meaning they aren't really a bad "investment" per se. It's like buying a vintage Porsche 911; sure it's expensive, but if you pay $50k for one, drive it a few thousand miles a year for 5 years, and then sell it for $60k, is that really that dumb?
No, what's dumb is a $17k gold Apple Watch that will be obsolete and basically worthless inside 2 years. THAT is dumb.