I waited to post in this thread, and I waited some more. My fiance really REALLy likes the look of me in a kilt with a non traditional hat, and I was watching to see what y'all had to say without me muddying the waters.

I think what we are seeing is if the kilt is being worn as a "bottom" just like surfer shorts or pressed wool slacks or blue jeans, it can sometimes work with a non-trad hat.

My current rule of thumb hinges on kilt hose. If I am going to wear kilt hose with the kilt I _might_ get away with a non-trad hat, but it takes some effort, as demonstrated by the wizard.

With socks other than kilt hose (and typically lace up boots of some kind) wearing a non-trad hat with the kilt can look OK to, though it isn't a traditional look at all.

The other time I waited was to get a pic of my own to contribute after the wizard's challenge.