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OMEGA INCREASED THEIR PRICES OH NOOOOOOOOOO
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Happy Tue luxury watch loverzzzzz

Time to DIVE into a deck.

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Rolex only holds its value because of the false scarcity game the brand plays. If you buy in the secondary market at a decent price, most watches will hold their value. Much like a new car, the biggest depreciation hit comes when you leave the shop with a new watch. If you want data, check out watchcharts.com.
Chief
Yeah, agree with other comments, the brands are of less importance than the specific models. The secondary market is pretty transparent (though Chrono24 is only showing asking prices). My advice is to find a good gray market person to work with.
Even Rolex and AP have models that decline in value in the secondary market - they have select halo models that hold value or increase. The only other brands I can think of is FP Journe. Patek also has models that lose value. Having said that, all of these brands hold value better than other brands, who will depreciate much more
Your best bet is going to be low production microbrands - most of the ones are going to be many multiples more expensive than those two companies (e.g., Journe, akrivia, Phillipe dufour, Murakumo, etc.) things most of us won’t ever be able to get even with significant spend histories
Correct - anything where supply is constrained. Dufour has made maybe 300 watches total in 30 years. Grönefeld makes runs of 188 mechanisms (and has stopped taking new orders even for unlimited pieces). Akrivia/Rexhep rarely comes up. If you need to sell those, you’ll find a buyer.
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Watches aren't investments, so I wouldn't worry about which ones hold value the best and just get the one you like
Like a car, buying preowned will save you quite a bit on depreciation and you’ll never have to ask the question “does it hold value well?”
Only buy new if you’re going to play the AD game.