I don't recall what thread it was in, possibly more than one, but I remember reading a few remarks about how horrid it was to wear a flat cap with a kilt. I also remember a wee bit of sarcasm surrounding those posts.

I'm just curious, is this just personal taste, or something more?

I'll be headed to the Highlands next year and want to start getting prepped now. I need to get a few nicer bits of clothing. The Southern California fashion of a kilt, zip-up hoodie, tee shirt, and flip flops wont cut it unless I want to stick out like a sore thumb. I'll be getting a nice pull-over and some button down shirts for my kilt wearing here and abroad. I already own a wool flat cap and thought it would be appropriate to take with me on my travels, but then I remembered something about not wearing them.

(Note: I'll probably end up wearing whatever I want as long as it looks smart regardless of people's opinions here, but, you know, might as well strike up a conversation about it if I can.)