In no way would I presume to know half as much as many on here I would have to reject this particular look. not on any one article but more as looking at is the whole picture so to speak...

My understanding is a kilt is the perfect pair of pants that can be dressed up or down depending on the rest of the articles you chose to wear with it. With that in mind you have to match the boots not with the kilt but with the shirt or other accessories. In this example the boots don't go with the shirt and that is most likely why the look falls short of its true potential.

That shirt would be nicely complemented with a set of ankle boots and any pair of socks you chose (even white) scrunched down. With those boots I would lean more towards a collarless shirt or even a jacobite shirt. The shirt is too far in contrast to the boots for the look to appear appealing to me. Thats not to say you cant wear high boots with that shirt just not those ones IMHO

Wow long post I now defer to the far greater wisdom of the rabble