Once the summers roll around, we prefer relaxation and comfort, which is why we all are big fans of pre-planned outfits. High-waisted shorts require very less preparation time, and there are plenty of ways to dress them up or make them more casual. Strappy sandals, sneakers, and even heels go very well with high-waisted shorts. However, you will fall in love with the longer lengths styled boots that look gorgeous with your shorts.