Thank you all for the excellent suggestions! And I am so glad many of you "get" the appeal of the silky cami + soft cardi/sweater combo. I will forge ahead with confidence when it comes to the top half.
Re: bottoms, OK, I think maybe I should have specified more in my original post. I am specifically hoping to wear skinny jeans with this formula. All of my jeans right now are skinnies. I am open to adding another style, like a straight-leg or slim boyfriend cut, but I'm soooo burned out on the search right now (buy-return, buy-return, buy-return, buy-wear twice-discard, etc.), I'm hoping to figure out something that will work with the jeans currently in my closet. So, Janet, that's why not a straight-leg or bootcut with pointy-toe booties...I just don't have any.
So Jessikams and others who mentioned sock booties...do you wear those with skinny jeans? Over the jeans or under the jeans?
And, JenniNZ, are these stylish Kiwis in their full-length jeans and ankle boots wearing skinny jeans? If so do they just tuck the jeans into the boots? I thought that was a no-no. My skinny jeans won't stay tucked into my ankle boots anyhow -- the boot shafts are too short and narrow. Maybe I need a slightly higher shaft bootie, like kkards suggests? But I'm still not sure how those are supposed to play with skinny jeans, except for the rolled/cuffed option.
Gretchen yes, I think you're right about color and/or pattern being a good bet. So, Well Dressed Guy, I don't think I'm looking for a "basic black" flat, as it turns out. I really like the idea of a metallic, like Molly Mac and several others mentioned. That feels festive/dressy/special, and could serve as a pseudo-neutral so they could easily go with multiple top/sweater combinations.
So, thinking about the shootie (omg Bijou I love those ones you linked to...a not-too-high heeled oxford in a interesting color/pattern/texture could be a great bet) / loafer / flats options. What do you all do about hosiery? I have to admit that nude knee-highs feel deeply unsexy to me. Perhaps in part because they inevitably fall down! Maybe shorter nude hosiery would be a better bet? Or like a fishnet anklet? But those wouldn't provide much warmth. You see the conundrum...
Really it's just winter that's hard! Once I can ditch the big coat, ballet flats are just fine with the rest of the formula. And in summer I can do sundress/cropped cardi/wedge sandals or ballet flats -- easy!
Apologies to those I have not mentioned by name -- please do not think your comments were less helpful! I'm just trying to capture/interpret the gestalt of the discussion without an even longer monster of a post...