Ankle Boot Mystery Solved?

I love ankle boots. I own 3 pairs of them. I have an issue with wearing them with jeans... I don't know how. Every time I put them on feel like it looks all kinds of wrong. I thought maybe it was a proportion issue ( maybe my legs are too fat ). 

After combing through tumblr, pinterest and the sartorialist I think I have found the reasons.
Jean/Pant Length. I think you have to have the pant skim the top of the boot or show a little skin to break up the line... or
Contrast and Color. I think the boot and the pant have to be close in color and contrast or it draws too much attention to your feet which when it's a block of color like a ankle boot makes it seem too heavy. If you choose to ignore this you must have straight thin legs, which I don't and won't have.
What do you think? Do you even think about this stuff? It's strange that I do considering that it's 9:30am and I'm still in my pajamas.

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