At risk of throwing the thread off on a tangent about what is "traditional" headwear, I know that a beret is not traditional highland headwear, but since I'm not a big fan of toories, I personally prefer the look of a beret (or caubeen) to the balmoral or glengarry for casual wear. For a dressier affair, I think it would be best to stick to convention and would go with the balmoral, toories be damned! (Glengarries would be another perfectly fine choice, of course, but not for me.)

This would just be my personal preference, and that said, I'm generally not big on headwear anyway....