I have a lot of different watches and I wear a lot of different ones. I have 8 in my EDC rotation that I wear Monday through Friday, and 3 others that I choose from to wear on weekends. My work week watches are all automatic and that's what I prefer to wear when I can. I get out a new one on Monday morning, set it and wear it the rest of the week. On weekends I don't wear a watch all the time because I might be working in the yard, working on cars, whatever, so I can't keep an automatic running. My weekend watches are all quartz, and right now they are all tritium which I have some use for in my irregular weekend schedules.
I mostly wear fairly large divers, with simple designs. I always thought divers would be tougher, big ones are easier to see, and if I'm wearing one while washing the car it shouldn't harm it. I'm not interested in expensive watches, but I don't look for cheap watches either. I can be happy with watches in the $100-500 range.
I never got into chronograph watches and have sold the few that I've owned. I've owned a few pilot watches but don't have any of them left, partly because most of them came with straps and I prefer metal bracelets. I've decided that if I found a good pilot watch or field watch with large dial, simple design and metal bracelet I would try that. Since I don't actually dive I don't need the dive bezel and taking that off would leave a larger dial for better visibility.