Cold weather is the constraint that most dress up games quietly ignore, and this one is built on it.
A winter outfit is really two outfits: the one people see outside, which is a coat and almost nothing else, and the one underneath that appears when you get somewhere warm. Both have to work, and the coat has to make sense with what it is hiding. Turtlenecks, jackets and proper accessories are all in the rail, and the looks that fail are the ones that treated the coat as an afterthought.