How to wear denim shorts outfit # 2. Ladylike Contrast To dress up my denim shorts, I added a cardigan with big gold buttons. I love the ladylike jacket trend but the boxy shape never works for my figure. I find the sweater/cardigan version to be more flattering since it drapes over the body. I’ve been wearing these sandals all summer anytime I want to be comfy and casual, but a little bit taller (I’m 5’3 and a half). LTKOver40 LTKStyleTip LTKFindsUnder50