When To Wear Shorts
1. The temperature should be hot and you should be in the right environment since your location plays into that as well. So in areas like Bermuda, wearing shorts actually with ablazer jacket is pretty common.
2. When you’re not conducting business or attending a formal ceremony/event. There are some guys in the fashion industry that I guess can get away with this but if you are conducting business or you’re going to be at a formal event, you need to wear trousers.
Better close than loose. The thing with shorts is that they only add bulk to the top part of the hips and the top thighs. And you don’t want to get the chicken leg look, and that will happen if your shorts are too baggy or they billow out on the sides, so try to avoid pleats on shorts unless you have a large hip area.
It affects the mood and the formality, so the short at the top left hand corner, those are the most common. Those are going to be the easiest to match. Once we start bringing in reds, blues, greens suddenly add to the informality. It becomes more fun and you’re going to stand out a bit more. Sticking with a solid and a traditional style pretty much any man can be able to pull this off.
What To Avoid
Shorts that are a bit too loud and short. They’re really drawing attention right to your crotch area and that’s really not where a gentleman wants all of the eyes in the audience to be focused on.
Shorts that look like swim shorts. I wouldn’t recommend it even if you were in the military.