26 Easy Ways to Style Your Favorite Shorts With a Pair of Heels

Figuring out how to wear shorts can be a major struggle, depending on the silhouette, and working them with heels may be 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 pull off this look.

The key is making sure that your outfit is proportional, starting with the style of shorts you choose. That might mean ditching your denim cutoffs and tank tops for mid-length shorts and tailored blazers for a more put-together outfit. If you're still struggling to picture the outcome, 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 feel inspired.