Well, that does not look like the dress for winter in Michigan, lol! Angie has done several posts over the last few weeks (months?) about boots with sweater dresses, midis, etc. You might want to browse back for some ideas. Also, every Friday she posts outfit ideas that a lot of people here take as sort of a challenge to try to do themselves.
I know nothing about this, but think jeans might be one of the harder things for you to wear, Ms Molly. Bootcuts might be your best bet there. But if that contradicts what anyone who knows anything says, go with them.