David,
I love those old Heuers. And they are valuable too. I think the watch to wear when driving, or anytime (no pun intended), is the one you like, whether it's a cheap or expensive one. However, the sort of person who is fussy and serious enough to invest considerable time/money in an impractical car (no, let's be realistic here) is likely to look for a bit of quality in a watch. It may be an unusual model, or an expensive one, preferably mechanical, but whatever you will enjoy wearing. As with cars, something that holds its value, lasts well, and gives you great pleasure, is always worth enjoying. Life is too short for anything less.
My 2c worth,
Dalton