Not necessarily. They have old car auctions for wealthy people (like Barrett-Jackson) where certain models really do fetch as much as owners paid for them, or

Not necessarily. They have old car auctions for wealthy people (like Barrett-Jackson) where certain models really do fetch as much as owners paid for them, or more. It's still a gamble, but I think your odds of at least holding your value with a classic car are much better than with a watch. I could be wrong of course; I know a lot more about cars than I do overpriced luxury watches, after all. But I suspect the watches are much more like diamonds: only "valuable" to the initial buyer (and mainly for sentimental reasons), and largely worthless to everyone else. (Yes, a resale market for used Rolexes and the like exists, but you're not going to get the same price for your 20-year-old Rolex as you paid for it.)