On the cuddle duds. I'm less than 5 ft, so even petite cuddle pants are too long. I just take them up above the edge (lacey ones too) about 2-3 inches (makes about 4-6 inches and do a machine stifch. If I want, I cut some of the bulk off, but haven't done my last ones. You will definitely need them. For that time of year, I would definitely have a fleece jacket (I got an LL Bean years ago). It didn't have a hood, so I made one in same colors. But they do have hooded fleece jackets. I also carry my london-fog type rain coat, it's hip length with a hood. for sweaters, I carry maybe 2 acrylic sweaters, because they wash and dry very easily, compared to anything made with cotton Then you can carry less sweaters. I spray all my outerwear including purses with Camp Spray, found in camping section of sports stores (not Sports Authority), or even supermarkets. It's stronger than Scotchgard. Doesn't fade clothes or shoes.
Shoes. I carry two pair sport shoes to walk, and have done so in much rainy, wet, snowy weather. I spray with a camp spray before I leave home; I start sprayig about 2 months out, three sprays, let them dry. The chemical smell goes away before the trip. That really helps keep them dry. On our first GCT river cruise, we took the pre-trip in Amsterdam in late February, and it was freezing cold; we walked every day we weren't touring into the town, even though the train station was just a few minutes from the hotel. It rained, snowed, sleet, and great sunshine in a matter of a few hours, then again later on--at least three times like that in one morning. We were out in it the whole time, didn't stop for coffee or anything.
So, layering with cuddle duds top and bottoms, jeans, or winter knit pants, long sleeve jerseys including turtlenecks or turtle neck "dickies", two sweaters in acrylic, heavier socks (look for the ones that keep feet dry and dry fast when washed. I found a long scarf is good for wrapping around the neck, and of course the gloves, hats. I waterproof all of these as well. Have a great trip.