You had me at *thumbnail* #9 --- you HAVE to keep this!
I love how it looks borderline boyfriend worn open with the jeans and then goes feminine with the nipped waist over a skirt.
I think the blue skirt was simply the wrong proportion to work with this --- what bothered me was the little edge of zip showing, not enough to be intentional but just enough to catch the eye and hold it.
The orange on the other hand... so chic!
I'm in the camp that says no worries to the back fit --- it really should sort itself out over time.
I think you found The ONE, Shannon --- and a clever, thoughtful SA in the bargain!