When we visited Paris a couple of years ago, I stumbled upon a shop full of the most gorgeous clothing. Maje is a French line of amazingly feminine but also impossibly cool attire. Each piece is perfectly tailored and embodies classic aesthetic, often incorporating a slight edge (you can snag a pair of classic jeans ... and a black leather and feather mini skirt). I wouldn't consider Maje an affordable line, but almost the entire collection seems to be on sale right now on their site. If nothing else, pick yourself up some inspiration from these pretty Parisian pieces!
Maje Sadly, none of their beautiful brick-and-mortar shops are in Chicago yet, but it is available at Bloomingdales at 900 N.