I'm coming back to this late, sorry to leave it hanging!
Tammyw, the top is from Athleta from about a year and a half ago. I think it was marketed as a rash guard, but I wear it for running and cycling too. It's a great top! I have matching board shorts too. I also love that color.
Greyscale, these would be for wearing with skinnies and the skirted leggings, maybe skirts (as rarely as I wear them). I wouldn't bother wearing bootcuts in the weather that would necessitate these boots. I would wear my shorter booties with rolled boyfriend jeans.
Angie, the heel height doesn't feel as high as it is. The wedge and slight platform sole make these extremely comfortable. They feel warm but not TOO warm (I have some old rain boots that are rubber and feel stifling as they don't breathe at all, and I don't like that feeling). There is enough room in them to wear substantial, warm wool socks too, which is good.
Sydney2, good point, and yes -- I can definitely just loosen and tighten the laces to put these on and off, which is good. It is not necessary to take the laces out of the holes at all.
Suz and Una make a great point about the climate I live in. We are not a big boots-on and -off climate or culture around here. I did a couple of on-and-off sessions with these just to see how much of a PITA the process would be, and it is not as bad as I thought it would be. It really doesn't take long. I don't anticipate needing to take off and put on boots like this during the course of a day -- I would wear them on days when I'll be out and about (going to my studio or running errands) so they would go on in the morning and stay on all day long, so really it's not a big ordeal. I would not wear them to go clothes or shoe shopping.
I do like how they look, which is rare for a winter-functional boot. I was a little worried about the covered wedge, and in fact, I usually don't like the look of a wedge on a tall boot, but for some reason, I don't mind it on these, maybe because the lighter grey panel provides some break to the expanse of long black boot.
I haven't decided yet. I initially wrote them off when I pulled them out of the box and saw there was no zipper, but after trying them on decided to give them more consideration. I liked them a lot more after trying them on. It's nice that I have a generous return window with Zappos! Thanks for all the feedback and opinions.