OK, I think enough people have responded that I can tell you what I think.
I like them so much better now that they're styled. I don't love them with the skinnies, but then again I don't really like any booties with skinnies, and these are actually better than most w/skinnies. Yesterday when I tried them on I had on the skinny straights I was wearing during the day, and they were also rolled up so I could see the boots. That did not work at all.
Shannon, I love the cutout ankle shape on booties (my black dressy ones have that too). My current red booties (that I'd be replacing with these) have a very straight and slightly gappy ankle so I don't think they look good with skirts. These are much better.
DJ, the toe shape doesn't bother me looking down. I think as long as my face is not five inches away from it it's fine. So looking from a normal position (sitting or standing) it looks proportional, especially with non-skinny pants.
Oh, and I did not move the camera, so I don't know why I appear taller. Maybe it's the silly blogger pigeon-toe pose (which is actually useful to see both the front and side of the shoe at once). =P But if I look taller, I should do it all the time!
Aziraphale, I was hoping you'd chime in! You are so right that they are super comfy. So yesterday J. said that the shape of the shoes was "ducky." He saw them in the box, not on my feet. That was kind of a weird description, but, thinking about it, it makes sense because my feet are actually pretty duck-like - flat, skinny in back, wider/splayed in front, skinny ankles. So these shoes fit pretty much perfectly. My toes are not cramped but the rest of my foot is not flapping around either. In that respect, they are much more comfortable than, for example, my Docs, which are so roomy on me (width- and depth-wise) it's ridiculous.
I agree about the necessity for red shoes! I am down to one pair (the Docs) from three (am ditching the other dead burgundy booties, and have demoted the red dansko mary janes to lab shoes) and definitely feel the need for at least one other pair.
ETA: Not really worried about datedness. I think they're pretty instantly recognizable as fluevogs, so kind of outside of any considerations of mainstream datedness or not.