Seeker80

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.

You might be able to get a pre-owned Hamilton Murph. It's a little easier to dress up, versus the other khaki field models.

Throw on a canvas strap, NATO, even a rubber strap for sports use.

Get a vintage-style leather strap, sailcloth or perlon for casual wear.

To dress it up, there's all manner of leather straps, but you could give mesh a try too.

Yeah, some will. I was wearing my old Geneve Dynamic, and a young guy at the drive-thru recognized that it was an Omega. He said those and Tag Heuer were good. I figure that might put him a bit above-average among non-watch people.