If you can fit the bulk of the bootie/ankle boot underneath the boot cut of the jeans, thats fab. You'll just be covering up boot detailing that you paid for - which is kind of a waste, but not a problem. Make sure you do the walk test too, though. Sometimes, bulky boots catch onto the back of jeans and it's awfully uncomfortable.
So it's sweet to see boot detailing when you sit down actually!
I wear regular thickness cotton socks - usually black. (I am not into seeing crazy sock patterns that clash with my outfit). Hose-like trouser socks are another idea, but I don't use them. I MUCH prefer comfy cushioning socks!
Beth, I'm going to answer your blog question on the blog