Just looking quickly at the photos, #5 works best. Although I agree, pass on this skirt if it is constricting. If you have doubts now, think of the doubts you will have when its newness has worn off.

As for proportions, I think #5 works best. The first look with a tucked woven shirt looks more corporate, not sure if that's your goal, and the proportions aren't as flattering as #5. As for the gray tops, there is something about pairing these longer tops with an above-the-knee flounce skirt that feels tricky to me. It could be that both of the gray tops need to be either longer or shorter to work with this particular skirt. I.e, if they were the length of the LE top they might work better. I think both grays are fine on you, go with what you like best color-wise. The light gray top looks like it would work well with sweats / yoga pants for an at-home comfy outfit. I could see the dark gray top looking good with dark wash denim.

In sum, the skirt works well with one of these tops. You might want to find another skirt that will go with a greater range of your tops.