Vintage watches can be great value, but keep in mind the (likely) cost of an overhaul.
I think for $250, I might go for a vintage Mido Commander for around $100, and spend the rest on service from a trusted watch-servicer. Mido uses top of the line (not in-house) movements. They're great value for the money in mechanical watches--aesthetics are subjective, of course.
For new, I think I would look to Seiko, Citizen, Tissot, Hamilton.
The best outcome for the OP...