This is a perfect example of something that's been bothering me. Scots have relegated the kilt only to a very few occasions, and probably because of this, they are very inflexible with regards to the wearing of the kilt for casual situations. Thus it has become a "uniform" of sorts, where only one type of shoe is acceptable!
I am of course not arguing that the Scottish traditions are 'wrong'. Just that they are so inflexible that it's no surprise Scots rarely wear their kilts!
As an American, not steeped in the tradition of authentic Scottish kilt-wearing, and approaching this question from more of an American fashion sense (which may be an oxymoron, I know), I think there are tons of shoes out there that look great for wearing with a kilt in casual/outdoor settings when boots are not necessarily called for.
I've found
these to be comfortable and stylish with a kilt. They're not too dressy but they're not too casual either. And with a decent tread, they're great for stomping around at Highland Games, festivals, etc. These are the shoes I was wearing when I got the mysterious "I really like your shoes" comment!

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