The one great (and simultaneously bad) thing about Chicago weather is that it never gets warm too quickly. It allows us to bring out our spring wardrobe's slowly while incorporating some of fall's staples as well. Lightweight jackets, sport coats with sweaters, and hoodies still have a place in our closet's rotation. Fun, light colored jackets are only appropriate when the spring is here. Otherwise, most of those colors in jackets are reserved for only post-retirement set who live in Florida most of the winter.
P.S. Dept728 makes a fabulous buff and beige fleece that you can see at http://www.dept728.com/jk1x.html