Layer up the Chambray Shirt Dress with a cropped sweater and some black booties. And call it a day. Tips: make sure your sweater hits above the waist of the dress so you don't look frumpy. Roll up the sleeves so you can show a bit of the dress underneath and pull the collar out from under the sweater. A heeled bootie allows you to transition from work to night and is a little more chic than a flat.?