I, for one, think that the flat cap looks just fine with a kilt, when worn in a casual style. I can't give any justification for why that is, other than -- to my eye -- it looks just fine. This is especially true for a tweed flat cap. I own a Harris Tweed flat cap, but I don't wear it very often because I don't think the style looks all that great on my particular head.

I don't really buy the argument that it doesn't look right because it does not have a toorie. I own a Highland bonnet (and have owned others in the past) that are made without a toorie, and they are very traditional items of Highland dress. And, of course, they look just fine with the kilt. As always, pictures are helpful. This one doesn't show the bonnet in all its glory, but you get the general idea:


I do agree with you about the beret, however. I don't think it looks quite right with the kilt, and it has nothing to do with the presence or absence of a toorie. The reason I don't like the look of it with a kilt is due to the fact that it somewhat resembles a Balmoral, but is not a Balmoral. So whenever I see someone wearing a beret with their kilt, the impression that I immediately get is that this person bought the wrong hat because they didn't know the difference. (This is evidenced by the fact that I frequently get people coming into the museum shop asking if we carry "Scottish berets" or "those berets you wear with the kilt.") Now, this is not true in all cases -- Jamie, for example, wears a beret with his kilt at times and he knows perfectly well the difference between a beret and a Balmoral. But that's just the overall impression that the look gives me.

My most recently acquired peice of headwear is a shire hat, made by Christies of London. I purchased this on a recent trip to Charleston, SC. It's made from Harris Tweed and I have a sport coat in the same pattern, as well as a kilt jacket & vest in a pattern so similar as to practically be the same. I absolutely love this hat and have worn it often since buying it. However, not with the kilt.


I couldn't tell you why I don't wear this with my kilt other than the fact that I don't think the style would look right. If anyone has contrary opinions I'd love to hear them. (I also don't generally wear it with my sport coat of the same tweed, as I think the overall look is a bit effected; I think it looks much better with a solid jacket, or one of a different pattern).

But when I wear my kilt, if I need headwear, I generally reach for one of my balmorals, or the tweed Highland bonnet mentioned above.