We would really need to see the movements inside the cases to give an accurate dating. Bases on case design, the more ornate one, I would guess, would be 1930's-1940's. The other one I would put at 50's to 60's. More expert people will likely chime in later, just my 2 cents.
The watch on the right is almost identical to a Bulova 9AT/10AT, which would be the 1920s or early 30's.
Automatics date to the late 1950s and into the 70s, and that style case looks late 50's/early 60's to me, but could have been sold during any of those years.
Other than the dial on the automatic, they look to be in very good condition, nice watches indeed.
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