I always try to match my boots with my belt. As I only have on sporran for the time being I wear that one (black) but I only wear it with my black leather UK or SWK Nightstalker anyway.

It just looks odd to me have boots and belts that dont match, or at least are not complementary.

I also wear over ankle boots with pulled up socks (and pushed down too, depends on the shirt/kilt combo) Generally for what would have been a 'jeans' outfit before the kilt its pushed down socks. For a 'slacks' outfit in BK (Before Kilt) its pulled up.