'Ultra' Casual Kilt Wear

[Nathan]

"Kilt as jeans"? I have no problem with the concept. But sartorial ideas of what to wear with jeans, at home or privately, vs. out in public, may differ. Would I, or do I ever, wear an untucked t-shirt with jeans? Sure. At home. Never, ever out in public.

The absolutely most casual I'd ever get with a kilt in public -- on a very hot day -- would be something like this:

Dale, your look is classic and smart and you are indeed a fine dresser. As a man who has passed my 35th birthday I am attracted to classic style more and more.

The classic look is not, however, hip or trendy. I think the OP is trying to bring the kilt into his regular style and that of his peers. In my generation, for example, casual shirts were never tucked in. Dress shirts were, to be sure, but casual shirt tails were left out with jeans.

There is a look of deliberately messy style that the keen eye can parse from someone who is just a slob. For example, a few years ago, it was popular among youth to use pommade products in their hair to achieve a "bed head" look like they just rolled out of bed after partying. If you inspect it closer though, you can see there's obviously product in the hair and the "mess" is arranged to flatter the face. The guy who actually did roll out of bed with his hair sticking up on one side, doesn't look as
cool as the guy who just evokes the look.

It's the same thing with wearing shirts untucked or jeans that come from the store with rips in them but making sure the outfit is pulled together with an obvious nod to cultural trends.

It is generational, but it's also about identity. If, like Kyle, you are aiming for Alex P. Keaton and have a conservative approach to your clothing, you would reject these trends as fads unworthy of consideration.

If, on the other hand, you're on your way to see an Arcade Fire concert and want to hand out flyers for your own band's upcoming show next weekend, you shouldn't look too "clean cut".

Some prefer their look to have an "edge". An iconoclastic middle finger (or two fingers for our British friends) to the conventions that came before. That's rock and roll and that is to a large extent Youth culture.