ConElPueblo
·If both were for sale at the same time in the same place, this is maybe true. But the market doesn't work like that.
It is dependant on what particular watch we are discussing.
The "Don Draper" as described by @Shabbaz is a prime example, as the main driver behind the relatively high price it commands is the group of new collectors who specifically seek it out, most of whom are looking for one good looking vintage watch to wear on special occasions. In opposition we have a watch like an Omega 33.3 Chronograph, which is a watch typically sought after by seasoned collectors who value traditional collector characteristics; the main buying pool of a Seamaster DeVille values differently and thus a redial (even a great one) of either will affect values differently.