Do heels and shorts go together?Heels plus shorts is not always a good combination. If your shorts are too skimpy and your heels are sky-high, it might come out too trampy. If you really want to pull that look off, make sure to wear colored (preferably dark) stockings or tights under your shorts. Flats and flip-flops look better with shorts for a laid-back, relaxed look. The proper length of shorts depends on your height. Make sure that the length of your shorts will be as long as the tip of your middle finger when you put your arms on your side.