I tend to wear either a pair of black loafers or a pair of black wingtips with my kilts. I'm usually rather dressy anyway so that usually looks great. I have to admit that I've always been tempted to get a pair of trooper boots, but I don't know how it would look with a kilt.
Mostly with my kilts I wear my Doc Martens I have a huge selection of Docs to choose from, with the casual poly/Cotton kilts that I make I wear my Airwalks or Converse.
When I dress up I have my dress shoes. Just recently I purchased I nice pair if Geronimoe( hope thats how you spell it ) boots that slip on .I look at where I'm going and coordinated which kilt, sporran, belt, hose, and shoes to wear. Sounds a little high maintanence. But I love it.
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