FT, the "evening" tops would be worn with the bootcut jeans and heeled boots most likely. Sort of a dressed-up casual. I would prefer to have a small collection of nice tops for our nicer dinners out so that hubs doesn't see the same blouse/top at nice restaurants every time we do one of those special dinners. As i said in my post, 5 and 6 are the same top, I just wanted to show the back detail.
Warm wool socks, a couple of tank tops, a set of long johns (a thin Uniqlo set), and some Uniqlo heat-tech tops will definitely go with me, as under layers.
Two cashmere slouchy berets are going with me (one black, one blue), and I'll take two pairs of gloves as well. Also a compact umbrella.
Lisa, I definitely want to take at least one of the 9-10 choices because those are the warmest and best in foul weather. Yes, 7 would be worn with the dress -- those will function as "dressy" shoes for this trip. Not terribly dressy, I know, but I think they'll work.
Cat, to me, "sweaters" are pullovers. I will wear those over one of those thin under layers (heattech tees). I don't really do cardigans. But I am thinking that one of my lightweight leather moto jackets would be a good layer -- perhaps the grey one, so I'm not adding more black. Thanks for the nudge about that. Re: shoes, I also don't really do ballet flats. My one pair of slip-on loafers are really more warm-weather things. I think I'l be fine without non-bootie shoes since I barely wear anything other than boots or booties in the winter at home, unless we're talking about sneakers. One of the scarves pictured is quite warm (the Missoni) -- I may take another warm scarf. I have a red one that might be good for sparking up the long black puffer. Or maybe my white faux fur scarf, which is also quite warm, but it's kind of bulky.
Suz, I'm taking the new long black puffer (see below), and now I'm thinking of taking my grey leather moto as another mid-layering piece. I'm not sure whether the weather might make bootcuts problematic, but if I'm mainly taking those for casual "evening" wear, I think it will be OK. I am thinking of adding one more pair of jeans though. Plus there are the jeans I will be wearing on the plane. So that would be five bottoms, total. We're staying at Marriott properties almost the whole time (yay for reward points!), so laundry will be an option.
Oh, the Aquatalias are a few years old and suede, and I've never done a thing with them even though they have been worn in slush and snow and salt. Those boots are a miracle! I'm thinking I might take those instead of the Ugg moto boots because they look a little more polished. Still thinking.
Thanks for the ideas, ladies!