answer:If he was a Scot or it was a cultural thing it wouldn’t bother me. My man has long, skinny, fluorescent light tube white legs though, so I think he should avoid anything too short. Benefits, air to their family jewels and a sense of freedom? There are health benefits, testicles are not constricted. The first two are especially true in hot climates. My husband said, quicker access to scratch said jewels (rolling eyes here) You can wear a kilt to most occasions. In fact, I am not sure there are occasions when you couldn’t wear say a kilt. Not sure about a skirt. It is very individual. With or without… whatever feels right. On a windy day, I would prefer men wore underwear.