I'm going through a phase where I'm completely blinded by the value in vintage watches. I've found fantastic watches for unbelievable prices. I'm now on the hunt for a Rolex Datejust. I can't afford one for retail let alone the current secondary market prices but experience tells me that with a little bit of patience I'll find a beautiful vintage piece within budget sooner rather than later.
Take a look at vintage Omega. Lots and lots of options there. Omega Geneve is particularly overlooked yet they are the quintessential dress watch so this makes them surprisingly affordable. You will find something for your budget, no matter how low you think it is. I speak from experience when I say the charm of vintage Omega will get to you. It's one of those things that you have to experience to understand. Happy hunting!!
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