How to wear denim shorts outfit # 1. Simply Classic You can never go wrong with a white button-down and denim (jeans or shorts). I love wearing this crinkled shirt when I’m with my kiddo because I never have to worry about wrinkles. I wore this exact outfit, just with my lighter denim shorts, during a heatwave to a playdate dinner. I felt super comfy all afternoon and evening. I also highly recommend investing in some type of flat cognac sandal if you don’t have one already. I wear mine all the time. LTKFindsUnder50 LTKStyleTip LTKOver40