Originally Posted by Class-of-2013
I certainly want a rolex, but the ones I'm looking at all range into the $8k - $14k brand new. Even at $5k, let's say I find one, I feel the value to "oh shit I spent too much on a watch" ratio is too great in my mind's eye. I'm liking the Sinn U1 though, very classy and seemingly well built and high quality.
A somewhat less mainstream suggestion: I've really been feeling my Marathon GSAR lately. It looks great either with the metal bracelet or a NATO strap (although the latter can't really be pulled off with a dress shirt) and even with the bracelet can be had for under $1K new. ETA automatic movement, and I defy you to break one. It is chunky though so you have to like the look.
If you like chronographs, there's also the CSAR...
But to the people who suggested an Omega Speedmaster that's one that I'd love to have someday, just that money could more easily buy me a motorcycle
Also something like a vintage Heuer Carrera, or if you think you could rock it a Monaco would be cool, but vintage brings its own challenges...