"I've said it before and I'll say it again; it is not that men's shoes look awful with a skirt, the combination simply looks different. Just as a man in a skirt looks odd to the majority.
If people are familiar with something, be it men in skirts or men's shoes with a skirt, it will look "normal" and no one will bat an eye. "
Yes, people do get used to what they see.
Please correct me if I am wrong.
It is however, a whole new kettle of fish, when you put a skirt on.
There is a big difference if the man is wearing a "manly outfit, with a plain manly skirt, bare, sturdy hairy legs, with norman men's shoes.
This will generally be no problem.
But think about seeing a commando in full combat rig wearing white sneakers.

It is the more free style that gets difficult.
A skirt extends the body line down, and the legs are the spindles which support the body. This is very different to the lines we are used to when wearing pants.
There must be some sort of balance there. If you have very large feet, and spindly legs, it will look out of proportion. That is possibly compensated by having bare legs, the light colour making them look bigger, better in proportion to the feet. Any skirt gives a whole different distribution to the body lines as compared to men's legs and feet in shorts. It is getting the lines to be "correct" for your feeling that is important. Shoes can make or break an outfit. Giving another effect by wearing tights, can also dramatically change the whole outlook of your outfit. Shadow and light usage. I am sure any architechts would understand. We are achitecturing our look every time we put clothes on. Getting a pleasing balanced look is not always easy.
So when the little tricks of the trade are applied, there are a multitude of possibilities available but it may mean having several different styles, soorts of shoes to make it successful. Even a round toe or a chisel or pointed toe can make a big difference. It can be a fine art at times. That is why we men who go freestyling, more than just the manly look, are looking for different shoes than generally available for men, to compleet our outfit. Women don't have so many shoes for nothing. ( some may


It makes a big difference if your skirt is a narrow straight skirt or a wide A model, accentuating in different ways.
If it was done right, then you should be able to see what the intention of certain styles was through the years. Accentuating certain looks or hiding certain shapes. Just like the ban the bra revolution, I assume dresses were flatter then than before. And so do shoes follow. But I still think that big feet and slender legs don't look so good. Wearing a slender shoe puts that look back in balance. "white" bare legs, making your legs look bigger, or dark black tight bound legs give a whole different look and can compensate for many things. All the while the end result is a "good look", the right balance.
We are not women, but the lines they have, are a very good guid line to follow. Understanding fashion, what it is that with certain styles is meant to be accentuated or disguised, may be the key to success or a less good looking outfit. And face it, wheather manly of more freestyle, we all want to look good. Irregardless of male or female.
Peter v