There are some seasons in some climates where shorts are not optional, so you need to minimize the damage if you can. There were actually Navy officer shorts that went with khaki uniforms, but I wasn't an officer, so didn't have that problem. There was no part of the enlisted sea bag that were shorts except underwear and a drab gray swim suit. In my twenties, I think I wore some "cut offs," and in later years, drag on some chino and cargo shorts when heat requires it. Men are destined to make clothing mistakes -- cowboy hats with sports jerseys, loafers with overalls, bolo ties with suits. Mostly, if you have a wife, trust her. The old joke: "I'll wear any damned thing I want to wear. What do I want to wear, honey?" Except as in brad's case with the overall cut-offs -- no, no, and no. On the other hand, dress codes and "unspoken" rules can be tyrannical, so sometimes you just have to wear socks with sandals or something that crosses the line, just to irritate anyone who cares too much about that stuff. At some mystical point on the time line, young people don't care what you wear, or for that matter, what you say, so take full and terrible advantage of that.