» Tue May 17, 2011 8:17 am
If you plan on it for formal wear:
Loose the hat; flatcaps are traditionally workwear (and if you don't respect tradition, why are you wearing a kilt?). Loose the day plaid, or get it in a different colour (possibly navy). If the day paid is not formal attire ( I don't know), then get rid of it, wear a navy blazer, a dress shirt, and a tie (plaid is pretty bold, so avoid patterns on the shirt, but a simple one on the tie would be fine). Loose the boots, get a nice pair of leather oxfords (black?).
If you plan on it for casual wear:
I wouldn't wear it casually- it's like wearing a suit casually, but if you insist... Loose the hat (or keep it; wear it only when the weather demands and doff it when you go inside/ take off your coat). Loose the boots, get a nice pair of leather oxfords (black, burgundy?), or leather boots (I'd avoid big army boots; maybe some ankle boots, or something more dressy; I've also avoid suede). Wear a plain coloured collared shirt. I don't really like a matchy-matchy with the day plaid and kilt so much, but it could work if you have a nice shirt.
To be honest, you look a bit like you're in costume, but your confident appearance makes up for it. Main issue is that it seems to be trying to mix casual (the colour) with formal (it's a kilt, matching bottom and upper).
tl;dr: Rock it with some better footwear, minus the hat, and a confident posture, and you can do anything (though I'd really recommend only wearing it when the occasion arises).