Well, my first kilt was a complete fluke- a Murray of Atholl MOD tank given to me by a good old friend. I had no ties to the tartan, but now I do because of my great appreciation for my friend's generosity. I have since acquired a Davidson kilt ( my dad's grandfather was a Davidson), which I happen to think is one of the most attractive tartans. As is common for many Canadians, I have ancestors, and have married into ancestors, of several Scottish clans. Another great-grandfather was a Patterson- the fairly recently designed Patterson Tartan is quite nice too- and my wife is a Cumming, which opens up several other interesting possibilities.
For me, it is a dynamic interplay between personal connections, and fiscal opportunities.

So many tartans, so little time.
Cheers,
John