If I bought a $50k watch, it would depend what I bought it for as to whether or not I wear it.
If I bought it as an investment, I would not wear it. Why? Well, I would invest in a watch because it would be an investment related to one of my hobbies. Some people invest in shares, I'd rather invest in shares related to my hobbies or in items related to my hobbies. For instance, I'd buy Ducati shares, even if shares in construction would be wiser. I'd buy Apple shares, even if Dell looked like the smarter bet. I'd buy a vintage Rolex, even if a first edition Dickens would make me a few quid more.
However, the ideal would be that I would have enough disposable income that I could buy a $50k watch to wear. If it were not something so important that my damaging it could remove a unique piece from the hobby, I'd wear it to destruction, if needed. Much like I would ride a rare Ducati on the roads, unless it was irreplaceable like one of Fogarty's championship winning pieces.
On the other hand, a Frankenwatch should be worn. This is why I don't get kasillion dollar reps, because I want to wear something I'd wear in gen if I could afford it. I'll wear a Fiddy or a 1665 (white) because I know I'd wear a gen if I owned it.
Oh, but if I did own a $50k investment watch, it'd make the occasional sortie for a fancy dinner. It'd be impossible not to take it out every so often.