I'm not a full time kilt wearer, and I haven't a large collection, but do feel I've got my bases covered. I picked up kilt wearing for two reasons; first, I think they look great, and second, I wanted another choice of clothing. I try to wear a kilt at least once a week, sometimed twice. This depends of cicumstance. Not being as hard core a kilt wearer as others I wear a kilt less in the winter than in the warmer weather.

As for the tartans I've chosen; My first kilt was a SWK Nightstalker. I chose this because it was affordable enough as a starter kilt, and the tartan, being a fashion tartan looked really good. I didn't want to spend a bundle to find out I don't enjoy wearing a kilt.

Next I ordered a traditional tank in a tartan I had a connection to, Clan MacKintosh. Being there were several different MacKintosh tartans, all of which I like, I let my wife help me decide which one to get. We settled on the modern hunting variation.

While waiting for this kilt to be completed, and realizing the need for a more durable knock around kilt, I went again back to SWK and bought a HW Black Watch. The intent was for this to be my outdoor kilt. Being wool I feel it would hold up better than my acrylic Nightstalker. This has become my go to kilt however.

As for starting out, I highly recommend SWK for a starter. The Black Watch is a universal tartan, and recognized by many people. I'd also recommend getting a heavy weight before you get a standard. The wool is really nice, and I believe it will hold up a bit better should you decide to use it in any situatio where it might snag on brush or whatever.

Tartan choice is always an issue, and often discussed on this forum. As you can see, there are lots of opinions. In a nut shell, it doesn't really matter.

I've considered a variety of other tartans for future kilt purchases. Isle of Skye, because it looks great. Scottish National, because it looks great. USCG tartan, because I'm a former Coastie. Any of the other MacKintosh tartans, because they look great and I've a clan connection. MacTavish Modern, because it looks great and it'd piss off KT(just joking).

Anyway, This is a bit of a ramble, but I hope it helps.