I have no problem with the kilt as jeans look. You can see some examples of how I did it when I fronted a Celtic Rock band in Ottawa in this thread:
http://www.xmarksthescot.com/forum/f...olution-79284/
A few tips here...
1) Try doc martin style boots, or hikers or something a little rugged and wool pit socks on the bottom.
2) If you're going to go with the converse, I'm not a huge fan of the white socks. Try ankle socks that disappear into the kicks and show off some leg. black athletic socks might also work better.
3) Watch your kilt isn't too droopy. The absolute lowest it should really go is mid knee. Many prefer top of the knee.
4) While I like the colour scheme, your "dressy" kilt outfit doesn't really succeed because to my eye, it looks like you're just missing some kit - A sporran and hose to be precise. At least with the "cool" look, it's obvious that you're going for a indie rock/hipster vibe. In that pic it looks like you're still saving up to complete a look. Some hose and flashes in a complimentary colour and your black sporran form the other photos would take that outfit up a few notches quickly. Actually, given the wristbands and belt a brown day sporran would be even more killer.. Nice kilt there by the way.
For the rock look, I also like a short leather jacket with the banded collar that has been trendy for the past few years. One of those would look pretty cool with your black leather sporran, some pit socks and black leather boots.
I respect where you're going and think there's a place for it, but I also think you'll find rather quickly that there are lots of occasions where a tweed kilt cut day jacket (braemar, crail or argyll) will suit you perfectly well.
The Prince Charlie is only for black tie affairs. A nice tweed, however, can be dressed up or down when a jacket is required to finish off the look. In the absence of a kilt cut jacket, I'd say don't wear one at all. You're better off with a pullover or a simple shirt and tie than a jacket cut for trousers, IMHO...
Anyway, your aesthetic is your own my friend. Enjoy. But I think you'll find it's great to be able to kilt out in any social circumstance. That means being able to dress it up or down as the occasion demands 
For other examples of people wearing the kilt in a similar vein, check out the band Seven Nations and early Ashley MacIsaac footage... for some ideas...
Good luck!
Last edited by Nathan; 20th May 13 at 09:34 PM.
Natan Easbaig Mac Dhòmhnaill, FSA Scot
Past High Commissioner, Clan Donald Canada
“Yet still the blood is strong, the heart is Highland, And we, in dreams, behold the Hebrides.” - The Canadian Boat Song.
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