I used to be with Don on the Casio front. I can't wear a watch (the wristband accumulates sweat and irritates my wrist) so I used to keep it loose in my pocket. Every couple of years I'd lose it, but at £15 for a cheap waterproof watch, this wasn't a big deal.
Eventually after I lost one, I realised I didn't actually need a watch anyway. Then I went for several years without any watch at all. If you need the time, there's almost always a clock somewhere - on your PC, in the car, on a shop down the street, etc..
Now I've got a mobile, I check that on the very rare occasions I need to know what the time is. More usually, I need something to remind me when it's time to do something, and the calendar on my phone does that for me.
As for Rolexes and other posh watches, they're emphatically not watches - they're jewellery. If you want a bit of attractive wrist jewellery, they're fine. But whether they tell the time or not is completely secondary to their real purpose, which is to look pretty.