The only time you have to worry about shoes is when you are going formal, and even that can provide you with interesting discussions.

To be quite honest, everyone I would ask on Prince's Street said that shoes were the least important part of the outfit. That meant that I didn't own ghillie brogues or formal shoes until the past year (meaning over 25 years of wearing the kilt) when I started wearing proper formal outfits.

I used to wear timberlands, tassle loafers, and pretty much whatever felt right.