I have enjoyed this thread. My approach to TCHD is evolving as a result of this forum. Disclaimer: I'm a bit of a dandy in all modes of dress, so I have a tendency toward that with TCHD as well.
For years, I only wore my kilt with a PC to Black tie affairs. When I started playing with a Celtic Rock band, I wore the kilt with high army boots, untucked button down shirts, t-shirts, football/soccer jerseys etc.. Basically anything rock and roll above the waist and traditional below the waist.
For the rare occasion that I had to look nice but not black tie I wore a collared shirt and pullover.
After reading this forum for a few years, I'm inclined to model my day wear style after the Highland Chiefs whose photos are posted frequently. I've started to accumulate the kit I see on them that I find the most striking. I don't like generic looking clothes. I don't want to have a carbon copy outfit of everyone at the event - see dandy point above. I don't want to appear costumed, but I do like to be dressed a cut above, always.
As such, I've been accumulating some nice things. My day wear will soon consist of a tweed jacket with braemar cuffs and epaulettes, a waist coat with pocket watch, a brown day sporran with seal fur accenting on the front, and patterned top House of Cheviot hose. Some might say it's OTT, but I feel like I'll be in good company having based the look on the Highland games attire of the Chiefs and armigers' photos I've seen here.
Colin, I agree with your point, not so much the less is more for me personally but the "let your personal style show through" point. I'm always just a little overdressed and colour coordinated, so I guess it only makes sense that I'll be so with my Highland attire. The trick is doing it well and not looking like a clown.
A couple of months ago with the ex-girlfriend.
Example from this weekend posted in another thread:

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