I have a version of those booties w/ the same heel from last winter: http://www.endless.com/Kenneth.....0027A8W2O/
They are SO comfortable and I wore them pretty much everywhere with everything from tights to jeans to dress pants, etc. They did not fit close to my ankle but I didn't find that to be much of a problem. I guess it made them a bit more of a rocker look. It took maybe two wears to break them in and then they were fantastic. I have really sensitive feet and feel every stitch and don't usually last in heels over 2 inches.
As a rule I never wear black booties or boots with no tights or leggings. I think it just looks funny against my pale skin, too high contrast. You can do slightly sheer or patterned tights though.
And somewhat related, Kenneth cole made the most adorable pumps ever with the same style heel that I am going to hunt down soon, navy or taupe? (own too many black shoes)
http://www.zappos.com/kenneth-.....ghter-note