OOh! I like both of these on you.
I've worn my Reports with socks and sockless and (briefly, at home, practicing before our trip) with tights; all worked. With socks, my straight leg trousers were covering the rather loose ankle of the boot.
I have mixed feelings about the looser ankle fit of these. On the one hand, it's a bit of a pain for skinnies (although some are wide enough to fit around the opening and just stay scrunched there, and others can be tucked as you have done). But it works great for straight legs, and it also feels cooler to me. When I wore these bare legged with a dress, I liked having that extra room, even though it might not be "ideal" to show a gap at the ankle, I felt it worked okay (considering my pale legs) because of the V design of the vamp and the taupe colour; the booties are a "nude for me" and actually allowed me to wear booties with a dress and bare legs, something I otherwise would not try.
The DVs would fit nicely at the ankle but the zipper would be somehow more noticeable with a dress. So it really depends how you want to wear them (and the comfort factor!)
Love the way both bookend your hair.