You’ll often hear that watches are “investments,” but rarely is that actually the case — at least when buying something new. Like cars, most watches depreciate once they’re sold, and with a few notable exceptions — hard-to-get Rolexes and Pateks notwithstanding — you’ll have to wait a very long time until they appreciate past their MSRP — if that ever even happens.
The silver lining here is that you can buy relatively new timepieces, made within the last couple decades, at a healthy discount. We’re talking thousands of dollars compared to the brand new prices. They may not be mint, but what’s an odd scratch or two?
TAG Heuer Monaco Caliber 11

What we like: When launched in 1969, the Heuer Monaco was not only one of the first automatic chrongoraphs ever made, it was also catapulted into the watch icon zeitgiest when it was worn by Steve McQueen in Le Mans two years later. The modern Monaco is fairly accurate to the original, boasting the same Caliber 11 movement as well as the same case and dial design
From the seller: Excellent case that shows very light wear; blue dial with original hands. The watch is running at COSC spec. Comes with box and papers.
You’ll save: $2,050