There are some that function quite happily in this category, and some that really.... don't.
Essentially this all comes down to how fragile the watch is, and the best examples of this are pocket watches. These watches are generally heavier than wristwatches, and when they get dropped, serious damage often occurs. F=ma. This is exacerbated by the fact that in many case, there is no shock system for these old balances.
Old wristwatches without shock protection are similarly at risk. We've all seen the old square, tank or tonneau watches from the 20s and 30s, basically most of these are sheet metal folded into a case. Despite any claims to the contrary, these watches are certainly NOT water resistant in any way shape or form, they are barely dustproof. Wearing one of these every day, depending on the environment, can be risky. Under the cuff of a dress shirt or taken out for special occasions, these watches can perform as expected, and that might be the best advice as to how to care for and respect these old-timers.
Old-Timers. HA! I think that might be a watchmaker's joke...
There are always exceptions to this, some 30s watch cases are very robust, but they will lack shock protection.
The Golden Era of watches is generally accepted to be the 50s and 60s, and most of these are good candidates for daily wear.
HOWEVER! Keep in mind what your watch IS, that is, is it a rare and expensive thing for which parts are generally unavailable? Some watches are literally Museum pieces.
When I first opened the shop away from the big city, we were still restoring 18 century Fusee and Verge Pocket watches. These are in general, extremely fragile, and I would always advise against any sort of daily wear, or any wear at all. They are generally much heavier than later watches, and parts for these are all hand made. I'm not saying they are not repairable, but I no longer undertake these repairs. Watchmakers who still do this type of work are few and far between, especially here in North America.
Also keep in mind, any water depth rated watches, even dive watches, may not actually conform to the original standard, and if they are valuable, I do not recommend diving with them. The official line from Breitling is that a depth rated watch must come in every two years for water resistance service, to maintain the water warranty. That also means no hot tubs or showers, which void these warranties.
The best analogy I can give is these old marvels of micro mechanical engineering are like old cars, treat them with care and respect.
I mean, you wouldn't daily drive your model A, now would you? Or go off-roading with your Willys Overland?
Ok, some of you would... but you get the gist.