After much studying this board, pinterest, blogs, etc. I sorted all my jeans, dressier pants, etc. into lengths, bottom widths, and leg tightness. I have found all these things make a huge difference (at least to me) in the type of footwear that works best with them. Then the process of putting on each pair, lining up all the shoes and boots,(hint to make this faster-one leg had one shoe or boot and different one on the other).
Here is my conclusirons of what works and what doesn't, at least for me.
1. With the bootcut that are wide enough to actually fit loosely enough over the boots, and the boots are narrow enough and low enough this can work despite heel height, and even with flats.
2. straight cuts are the hardest, and have to be judged on an individual basis. Was disappointed that one of favs, basic grey that fit so well, did not work at all with my new wedge booties-just too much bottom density (if that makes scense)
3. The skinnies look best rolled above booties, but look best slouched a bit with flats and oxfords.
4. Am also starting to love the look of socks with the rolled skinnies, and will incorporate this as the weather cools.
would love to see photos and hear your take on this subject.