That's definitely a classic choice.
I think there's a watch that would work at every price point from $50-$millions so that'd be the first step. The linen face rolex Jacob got is a choice I can get behind. Or a linen faced classic tudor.
I've been obsessing over old Breitling Top Times, and he has a nice one, but it's on hold: http://www.piecesoftime.net/salesww_pages/2050breitlingtoptime.html