Personally, I don't think the size of your braces would matter considering a kilt that fits right should stay up on it's own.

Back to the question, I've been known to sport a closely shaved head or an extremely cropped mohawk from time to time. I also like to wear Corcoran jump boots with my pant cuffs rolled up. However, I never wore braces, a satin bomber jacket, listened to oi! music or considered myself a skinhead of any kind. A few times at punk shows people thought I was a skinhead, though.