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I initially considered a two-watch collection with this mythical $25,000 budget (Okay, my rose gold A. Lange & Sohne 1815 and a black dialed Explorer II 16570 ended up a few thousand dollars too expensive – was a mythical loan also allowed?). Still, I know myself, and two watches just won't best watches around 5000 cut it for me because I will surely get bored. I think time and experience will eventually hash that collection out, but if I'm forced to choose the watches today, then I'd go with the following four.

No surprise on the Daytona winning this one. It's one of the most coveted watches from one link of the most coveted brands. You can see why. It's beautiful; it's not overworked, it's the right size, it's bling without being in your face.