American Eagle sweater (similar - on sale!) | Old Navy men's flannel | AG jeans | DV by Dolce Vita oxfords via T.J.Maxx
As soon as the cold weather hits, I start wearing the flannel/button-up under a thick sweater combo almost daily. It just works and I can't even think about wearing anything lighter than this when I'm getting dressed in the morning. Today I even wore leggings under my work pants. I'm pathetic.
The shoe switcharoo works really well in the winter. You can instantly make a cozy, casual daytime look appropriate for night by adding a pair of heels. It always amazes me how much an outfit can be transformed by simply switching out your shoes. Maybe that's why I have a shoe problem. ;)