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

IWC Portugiese Chronograph

What we like: Thanks to its incredibly balanced and refined design, the Portugieser has been a perrenial favorite in IWC’s lineup since it launched in the ’90s. In fact, it’s so good that it’s barely changed since. Technically, this model from Crown & Caliber is a different reference than the model sold today but you’d be hard-pressed to find any real, discernable differences between them.
From the seller: Watch is in excellent pre-owned condition with only a few faint scuffs on the case and some minor wear to the leather strap. Comes with original IWC papers and manuals as well as a cleaning cloth.
You’ll save: $2,200

Rolex Explorer II

What we like: The Explorer II here is the reference 16570, the predecessor to the current Explorer II made today. While it may be an older model, it looks nearly identical to the modern reference — though at 40mm, it’s actually 2mm smaller than the current watch. If anything, we’d say that’s an improvement.
From the seller: Comes with 2-year warranty.
You’ll save: $2,450