Is a Bowler acceptable

[Bob C]

I'm kind of amazed at how many people, those who desire to be accepted in a kilt, were ignorant enough to tell you not to wear a hat...

We're ignorant because we responded to a call for opinions? Wrong.

[Nick]

I think a bowler/derby would look best with a waistcoat and jacket, but in my mind they've always been hats worn with suits of one form or another. YMMV.

I've been trying to figure out how to fit a 1930s or 40s style fedora with my kilt. I wear a crushable felt fedora with the kilt all the time, with the brim snapped down in the back, but the up-snapped brim is giving me a bit more pause.

A homburg, now, would look great with a kilt suit with jacket and vest, and an Inverness cape, with a cane or umbrella. Sort of a Conrad Veidt-meets-kilt.