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... now I need to do the boots, which I know when new where black...
But! I want to paint them so they look well worn, any ideas on where to start...
Thanks.
You could start with a medium russet brown color and add a black oil paint wash over that.
I would undercoat the brown using an acrylic like Citadel (Games Workshop) "Beastial Brown." I'd use black or Payne's gray artist oil paint thinned with mineral spirits over this. I'd mix this bit "thick" and use a clean brush to take off most of it leaving the brown showing through on the high points (almost like reverse dry-brushing).
After this dries for a day or two, you could add some pigments that match your ground work colors or dry-brush those same colors on, but not too much so that the work on the worn leather still shows.
I'm sure there are other techniques that would get pretty much the same results, though - black boots with brown leather showing through on the high wear points. However, if you play with the colors (the acrylic undercoat and overlaying oils) this is a good technique for painting a lot of leather items from brown leather jerkins to black boots and just about everything in between.
HTH,