So I took overnight to think about this.
1. I don't feel fab in the red skirt when the top is tucked (except in the case of that one black shell). I feel only being able to wear an untucked sweater over it most of the time limits it. I may chalk this up to a buying mistake, but I am going to put the skirt into holding till next winter and see where my body's at, most likely. I suspect I should size up on these skirts so the waist is not at my chest, in the future.
2. I realized have a need for a dressy cold weather capsule, starting this year. We upped our membership at the Met Museum to the level where we get invited to nicer occasions, and we've been taking up the invitations.
Therefore, I can see a place for the black polka dot pencil skirt in my life, and believe it will be easier to style. The bloating is an issue, but I can do (and should be doing) things to manage it, especially if I know in advance that I'll be wearing the skirt. The skirt wasn't tight across my belly, and I'll likely always have tights or nylons underneath, which will help.
I also thought about how much I love red, and have very little of it. So... I'm going back for the skirt and the red version of the sweater I tried on. I will also keep the black top, as I believe I can wear it to work with jeans, or dress it up. I'm holding off on deciding about the silver top - I like it, but I will always need to layer over it during the festive season!