Okay, here is a better visual of the tall version, in all my over-pronating glory. I do not have doubts about the Chelsea boots part. And I can sit in these comfortably (am doing so now). The issues are whether they are too tall for me and whether the slouchy shaft is a deal-breaker. I don't mind it because it adds a little bulk to my chicken legs, and I think it's inevitable with my skinny calves, unless I got a stiff leather boot like the Frye Campus boots - but those styles are always too wide and straight for me. Having a leg-resenting moment.

One shaft is slightly lower than the other probably because that's the one I've been trying out.

I'd wear the tall version with dark skinnies as Rae said, maybe short skirts and dresses with tights, and the short version with skirts, dresses, and under trousers.

These would replace my OTK flat boots, which I rarely wear because they are flat, and possibly the DV Jousts when they give out.

I am totally open to all feedback.