(updated 10.28.2015)Unlike many kilt-wearers, I am in this for the everyday wear. As such, the fancy, $1500 wool kilts aren't exactly viable for me.
My current collection includes:
Utilikilts Workmans model - tan (retired)
Utilikilts Workmans model - chocolate (replaced above kilt)
Utilikilts LTD ED Survival - black. I won this kilt in 2008 as the third place winner of the Mock-U-Mercial contest. I believe something like five were ever made.
5.11 Tactical Duty Kilt (TDK) - black
Sport Kilt Original - large - Blackwatch.
Sport Kilt Original - medium - All Ireland (almost too SHORT for me, but great for warm days)
Buyakilt.com - Budget 8 Yard w/ Fly Plaid Irish Heritage - this is the kilt I got married in!
Buyakilt.com - Budget 8 yard Irish Heritage - same as above. Now I have a spare.
Heritage of Scotland Casual 8 Yard Douglas - A great 16oz every-day kilt
Each kilt has its ups and downs.
The Utilikilts are extremely durable, machine washable, they have pockets and I don't feel bad at all about thrashing them consistently. Of course, of the kilts listed here, they are also the most expensive and least traditional-looking. That tends to make them more easily accepted by people and also makes for an easier transition for people who are looking to get into kilts for the first time.
The 5.11 is a different take on the utility kilt concept, and was originally made as an April Fools JOKE! The company got so many orders for it, that they eventually relented and put it into limited production. As far as I can tell, they do very small runs of these kilts every year. They are light-weight and good for warmer weather, hiking, etc.
The Sport Kilts are a good way to get into the idea of wearing tartan and are my go-to for hot summer days. They are THIN and very light; probably only three or four yards of fabric total. They have a low-maintenance velcro closure system, so they go on and come off the easiest of all my kilts. They do not have the signature "swish" of heavier kilts with more fabric, which is usually just fine, but feels different.
Both of my more "fancy" kilts from Scotland are what most people think of when they think of the Kilt. They are 8 full yards of fabric. They sit about even with my belly button, whereas all the other kilts sit on my hips. It takes a little getting used to, but is not an unpleasant feeling. They have a more involved buckle closure system, which takes far more time to put on and take off than the snap or velcro styles made in the US.
That being said, they look MUCH more fancy and are equally at home at the local pub or at the fanciest restaurant/event in town, depending on the level of accessories you wear. These guys go on sale a couple times each year for the $45-$80 range, which is when I choose to buy them.
Speaking of Accessories...
Dressing up a kilt isn't as dependent on which kilt you wear, as what accessories go with it. The fanciness of your Sporran, hose, Sgian Dubh, vest, jacket, hat, footwear and all that makes the difference between going out to the local bar for a pint and going to a black tie event. You can wear the same kilt to both, but you would probably accessorize differently.
Kidder Bros "Loch Ness" in black leather. This is my every-day sporran. I wear it with any of my tartan kilts and sometimes with the 5.11. Highly recommended!
Buyakilt.com "Black Full Dress" with the fur and the dangly things and the silver cantle. This is my dress sporran and I wear it only to formal occasions (like my own wedding)
These I am less picky about unless it is cold. I got my cold weather socks from Utilikilts. The 3/4 grey socks they sell are HUGE and very warm. I have a couple other pairs as well, but they're just big socks to me.
This is an area where I am sorely lacking. In a utility kilt, I generally don't wear flashes. Just a rubber band underneath the fold of the sock works great. I have a matching set for my Sport Kilt All Ireland, but don't wear them much. I would love a few different colors of plain flashes, but haven't ponied up the cash yet.
A little less traditional here, I carry a regular folding knife in my boot every day. No need for the sock knife when you have one in your boot. Plus, most of the Sgian Dubhs that I have seen are cheap, pathetic imitations of knives. The HK P30 Assist works great as an actual knife, not just an accessory.
I do have a "safety" Sgian Dubh, but I almost never wear it.
What I would find more useful is the Sgain Bru, which is a bottle opener!
When I'm dressing all the way, I'm also in a tie (see the best tie knot for the kilt), vest, jacket, etc.