Pocket clocks, commonly called "watches," are curently out of style and are considered "old fashion" by many people who believe that only a trendy, plastic and quartz, wrist watch can succesfully meet the timekeeping needs in these fast paced days of the new millenium. Those of us who know better though, know that there is no chronographical need that can't be met by a good old mechanical pocket watch in the hands of an experienced user.
Now, I don't want to get into another "digital vs. analog" or "self-wind vs. battery" debate, but I think you should pick what you are most comfortable with and what would best fit your timekeeping needs.
Now, as far as pistols go, a Glock 29 strikes me as too big for pocket carry, even with big pockets. Sure, you could probably find a pocket large enough to hold the pistol, but would you really find it to be comfortable and secure for all day carry?