I was in Orlando for a week recently at some of the parks, and saw 4-5 guys wearing ladies watches. I don't know if they chose their watch or if it was provided by someone else, some were the workers in the park that looked like they were pressed into a ladies watch. Probably the most outstanding choice was the Ladies Timex Ironman, one white, one blue, and one pink:
One was the black leather Carriage Indiglo; I got a good look and recognized it; I have three myself:
One other was on the wrist of a guy, with his wife (no watch), I have seen some CD's wear this one as a favorite:
I suspect the ladies that placed these watches, if that is indeed what happened did so out of necessity than for fun.