Don't call it a skirt

While all of this applies to women too, it's harder to get men to think about the practical usefulness and comfort of skirts, so this is directed at the men.

"Self-respect is the noblest garment with which a man may clothe himself, the most elevating feeling with which the mind can be inspired." - Samuel Smiles

I know that for some men in our culture, the idea of wearing something commonly seen as women's clothing is a Very Big Deal, so let's get over that hump first. We aren't talking about wearing women's clothing here. We aren't talking about cross dressing. Hey, if that floats your boat, then go for it, but I look lousy in a sundress. What I am doing is inviting you to consider wearing a traditional MALE garment. Alexander the Great conquered the known world in a skirt. Think about it.
In modern Western Civilization, the appearance of a man in a skirt - unless that skirt is part of some kind of costume - engenders a range of response from total disregard to curious inquiry to obstinate denouncement. Masculinity is a fluid term, applied to men across class and racial backgrounds. It is a product of society's need for classification to keep people in constant relation to each other. Masculinity serves a useful purpose, but it creates problems by creating standards of thought, personality, and fashion for all men, regardless of other forms of individuality. This is the problem of clothing, and there are many books on the subject. Because we wear clothes and no longer have access to sexual and gender clues, our clothing takes the place of these cues and being able to classify people as the appropriate gender according to their clothing has become second nature in our society. Anyone who violates the common perception of these gender cues will generate a little attention - no matter how flawed or uninformed the common perception actually is. The common result is that even many men are confused about how to play out their own gender roles.
Even some men who wear skirts are very insistent that they aren't wearing a skirt, despite the obvious fact that they are. I mean, if you're walking around with a turtle on your head and someone asks you why you have a turtle on your head, then to say, "It isn't a turtle, it's a tortoise.", isn't useful. You haven't made any real distinction or answered the question of the inquirer. But, if it makes you feel better, then go right ahead and play the semantics game. Don't call it a skirt, it’s a Kilt!