I seem to recall a picture of Andrew Carnegie (ya know, famous philanthropist, and immigrated Scotsman who basically created U.S. Steel) where he was wearing a kilt that was most definitely stars and stripes. The apron of the kilt was the upper portion of the flag that had the stars, and obviously the stripes started across from there. Whether or not this was an artist embelishment or not, I do not know... but there was definitely no disrespect in the portrayed attitude of the wearer. Likely, Carnegie is one of the most highly regarded Scottish-Americans. Not that I would wear a flag-kilt, but it shows that there might have been a historical precedent for such a thing.

I too am under the impression that it is all about attitude. Although with some, it may help to have the kilt a solid colour, and keep the flag design on the front apron.