Popsugar Fashion Street Style How to Wear Heels With Shorts 26 Easy Ways to Style Your Favourite Shorts With a Pair of Heels 23 July 2019 by Nikita Charuza Image Source: Getty / Edward Berthelot 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 favourite 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. Related: 7 Fresh Ways to Style Shorts Like a Fashion Girl Pair Your Denim Shorts With a Puff-Sleeve Top and Slingback Heels Image Source: Getty / Claudio Lavenia 1 / 26 Style Long Shorts With a Silk Blouse, Headband, and Black Heels Image Source: Getty / Matthew Sperzel 2 / 26 Style White Shorts With a Printed Top and Red Heels Image Source: Getty / Christian Vierig 3 / 26 Style a Silk Cami With Denim Shorts and Orange Heels Image Source: Getty / Christian Vierig 4 / 26 Pair Your Bermuda Shorts With a Sleek White Blazer and Bedazzled Heels Image Source: Getty / Edward Berthelot 5 / 26 Style White Shorts With a Belted Blazer, Sunglasses, and Beige Heels Image Source: Getty / Timur Emek 6 / 26 Style Bermuda Shorts With a Bucket Hat and PVC Heels Image Source: Getty / Christian Vierig 7 / 26 Style White Shorts With an Animal-Print Top and White Heels Image Source: Getty / Christian Vierig 8 / 26 Pair Biker Shorts With a White Sweatshirt and Red Heels Image Source: Getty / Christian Vierig 9 / 26 Style Beige Shorts With a Belted Blazer and Brown Heels Image Source: Getty / Matthew Sperzel 10 / 26 Style White Heels With Tie-Dye Shorts and a Matching Shirt Image Source: Getty / Christian Vierig 11 / 26 Style Square-Toe Heels With a Blazer and Baggy Denim Shorts Image Source: Getty / Claudio Lavenia 12 / 26 Style a Two-Tone Top With Black Shorts and Simple Heels Image Source: Getty / Kirstin Sinclair 13 / 26 Pair Your Bikers Shorts With a Blazer and Red Heels Image Source: Getty / Christian Vierig 14 / 26 Style Leather Shorts With a Striped Shirt and Red Heels Image Source: Getty / Christian Vierig 15 / 26 Style Your Denim Shorts With a Button-Down Blouse, Trench Coat, and Lace-Up Heels Image Source: Getty / Christian Vierig 16 / 26 Style Black Bermuda Shorts With a Pink Jacket and Ankle-Strap Heels Image Source: Getty / Jeremy Moeller 17 / 26 Style Yellow Shorts With White Heels and a Purple Top Image Source: Getty / Jeremy Moeller 18 / 26 Style Jeweled Heels With Baggy Shorts and a Plaid Blazer Image Source: Getty / Christian Vierig 19 / 26 Style Denim Shorts With a Checkered Blazer and Black Heels Image Source: Getty / Matthew Sperzel 20 / 26 Style Black Shorts With a Bodysuit, Oversize Blazer, and Strappy Black Heels Image Source: Getty / Kirstin Sinclair 21 / 26 Style White Shorts With Strappy Black Heels and a Yellow Top Image Source: Getty / Jeremy Moeller 22 / 26 Style a Striped Button-Down Over Shorts and Jeweled Heels Image Source: Getty / Kirstin Sinclair 23 / 26 Style Light-Wash Shorts With a Plaid Shirt and Ankle-Strap Heels Image Source: Getty / Christian Vierig 24 / 26 Style White Shorts With a Colourful Sweater and Orange Heels Image Source: Getty / Kirstin Sinclair 25 / 26 Style Black Shorts With a Brown Jacket, Orange Vest, and Black Heels Image Source: Getty / Edward Berthelot 26 / 26 Street StyleShoesHeels