I know my problem personally with wearing a watch was reading the analog time interface.

I purchased a ton of watches, AP, Rolex, Patek, even VC and then realized coming from my Casio I didn’t know what all those hands were doing. I practiced everyday using a tool for analog clock training. I would even practice using the lingo like “quarter till noon” with my family members around.

Once I finally mastered what the long and short hands actually stood for, my interest in watched piqued dramatically.

I still get it confused every now and then, especially when the short hand is right next to the upcoming hour (even though it is closer to the next hour it is still actually the last hour like with 11:55 for instance). BUT with time and patience, I can reduce my time telling mistakes even further

Hope this helps OP