Perhaps it is a generational thing, as studies actually indicate that fewer young people wear watches than their older counterparts. My mother, who always wears a watch and who feels it is imperative for a responsible adult to wear one, made me wear a watch beginning when I was a freshman in high school. I wore a watch daily without fail for 4 years. When I went to University, I took it off and haven't worn one since. I didn't like it when I was a teenager, and I don't like it now. I do wear bracelets, and I don't know why I feel comfortable with that and not a watch, but watches just aren't for me.
However, anything will become habit if you do it enough, even if you don't particularly like it. I did feel like I was missing something when I would forget a watch while in high school, much like the sinking feeling you get if you think you have forgotten your purse somewhere.