Let's see the red PC again!
Wearing a kilt to an event where I'll be the only one is OK with me as long as it is appropriate to the level of dress, acceptable to the host, etc. I would generally go with Matt's wise words regarding when to keep it simple and when to get flashy.
Let me give an example of why I would now dress to impress a bit less in a crowd of 'penguins.' A couple years ago, I was in the wedding party of buddy and he asked me to kilt up. The rest of the groomsmen were in tuxes and I wore a kilt, horsehair sporran, and Braemar jacket but the same waistcoat, bow tie, shirt, and shoes as the rest.
I think the horsehair sporran was really too much for that crowd... some people were confused, others curious, and some downright offended. In a social situation where people are not familiar with Highland attire, that much hair in front of ones groin can certainly raise some eyebrows!
Or maybe it was the white hose... pity I didn't know better yet

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