Dude, I think you've got this kilt thing DOWN brother!
First pic: love it. Especially the flat cap. I love how it's slightly squirrelly on purpose. It WORKS in my opinion. Don't listen to anybody telling you otherwise.
Second pic: I don't think I'd wear the patchwork flatcap on the second look but, I LOVE the matching tie and hose!!!! KUDOS. Bold choices and it WORKS.
You've got style sir! Bravo.