this post was submitted on 17 Nov 2023
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That's a great budget to throw at something pre-loved.
Easy choice would be an Omega Seamaster 300 or Speedmaster. Maybe look a little harder for a Heuer Monaco or Cartier Santos.
I'd probably try and take my chances and get a foot in the door with a Rolex. Oyster Perpetual or Air King.
It's even easier to split the budget between two that aren't quite grails but are still quite good(ex: used Tudor Black Bay & Oris Big Crown Pointer Date), but I'd be here all day listing those.