One should note that the “dress” fedora came into existence when Americans stopped wearing fedoras as part of regular male clothing. That would have been in the 1960s. Before that, fedoras were an un-dress hat, or as we call it a weekday hat. Americans are apparently starting to wear hats again, and one wonders if the growth of small non-fancy fedoras will impact on out choice of hats (perhaps shifting more to hamburg or even back to top hats???).
A dress hat among Orthodox Jews would tend to “big” since we don’t use cars on Shabbos, and the argument against a big hat is its inconvenience in cars or other motorized transit.