Admission: I love kilts.
They seem to be one of those things that you either love or hate, and I just love 'em. A lot of people who love them like them due to the comfort factor, but that was never a big selling point for me since I just don't wear pants that I find uncomfortable. Skinny jeans? Absolutely not; I hate anything clinging tightly to my legs like that, so I don't wear them. The guys who talk about how "liberating" kilts are, I have to wonder why they spent so much their lives choosing the wrong pants.
Anyway, I'm very much a non-traditionalist when it comes to wearing the kilt. I don't think you need to go all-out authentic Highland getup every time you step out in a kilt. Just wear it like you would any other pair of pants. There are a few exceptions, though. I tend to wear hoodies when it's cold out, and I can't pull off a hoodie with a kilt without it looking a bit like a girl's school uniform. I don't have any sort of formal getup to go with a kilt, but you can get all kinds of fancy with it.
Accessories are a big part of kilt wearing, too. Some people are sticklers, like you *have* to wear flashes or a particular kind of shoe. I think that sporrans (the purse thing) are pretty much necessary unless you have a fancy kilt with pockets. I also think that they look weird without some sort of belt, but that's a personal opinion; the belt is pretty much only cosmetic since kilts are held on with straps. Those are the only two "must haves" in my mind.
The best kilt accessory I've found?
It just goes so well...
I can't believe that I never saw this, or responded to it.
Kilts are about the best garment in the world. As to wearing pants that are uncomfortable, I haven't been able to find a pair of pants that are truly comforting and not constricting in some way, which is just one reason I love wearing a kilt so much.
I personally prefer wearing the great kilt over the little kilt, though both are still great. I'm also not a stickler on having to wear ghillie brogues, or flashes (unless I'm dressing up). I actually wore my kilt to this year's Pascha service.
Also, I have worn my little kilt in three deserts, but the great kilt in one. They are great at keeping you cool, and all of the extra material on the great kilt is great for keeping the sun off of you.