Figuring out how to wear shorts is a major struggle, and styling them with heels is an even bigger conundrum! Sure, it's easy to slip into a denim pair with flip-flops when you're heading to the beach, but how do you get away with wearing them with heels in places like the office or even on a date night? While the idea of styling your beloved denim shorts with a pair of high heels seemed comical at one time, it's now become a street-style favorite in both the Summer and Fall seasons. With biker shorts and Bermuda shorts making a comeback, it's actually become a whole lot easier to wear this look. The key is making sure that your outfit is proportional, starting with the style of shorts you choose. That means ditching your denim cutoffs and tank tops for midlength shorts and tailored blazers for a more put-together outfit. If you're still struggling to picture this and need some proof that it can work, we've got you covered. Read on for 26 ways to wear your shorts with heels and prepare to get inspired.