Do pilots really wear "pilot's watches"?
High end mechanical pilots watches are very little use in the cockpit whether you are in a commercial airplane or a cessna 152. I love watches and I've searched for years for a watch that was a) very cool looking and b) actually useful when flying and I haven't found one yet. They usually fail on b) because their analogue chronometer and/or timer functions are very hard to interpret, and cannot be read at night. The digital readouts on the analogue/digital types are often small and rarely have lights for night flying. Some have lights that will only work when in calendar mode, which is about as useful as a chocolate teapot. Often the functions are hard to use and require a fair amount of fiddling to get them to work, which is not good when you have a high workload. 

Commercial airplanes are usually so full of technology that a watch is completely redundant anyway, so for commercial pilots it's a matter of style. I'm not a commercial pilot, I fly older light aircraft with less technology, so having a watch with timer and chrono functions is handy. For this I wear a Casio G-Shock as it has a large and easily readable face, a light activated by its own button, simple to use, and very rugged. Digital kitchen timers also work very well.