A friend of mine bought a Rolex Air King about 25 years while he was in college. Paid $1200 (and financed it for $100 a month for a year).

He wears it every day it, to every occasion, and it looks phenomenal. Recently, had it appraised in the $5000 range. He's beat the S&P many times over, not to mention the value he's received of having a nice watch every day.

Yea I get, it's not for everyone. But they're not the worst investments and they're truly beautiful machines. In the words of Ferris Bueller, 'if you have the means, I highly recommend picking one up.'

And for the super skeptical, here's a video of a man who bought a Rolex GMT Master in the 60s for $120 and had it appraised in the $80k range (despite decades of heavy use). https://www.youtube.com/watch?v=li0mRLcGbU8&feature=youtu.be