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.
How to Wear Heels With Shorts
26 Easy Ways to Style Your Favourite Shorts With a Pair of Heels
Image Source: Getty / Edward Berthelot
Pair Your Denim Shorts With a Puff-Sleeve Top and Slingback Heels
Image Source: Getty / Claudio Lavenia
Style Long Shorts With a Silk Blouse, Headband, and Black Heels
Image Source: Getty / Matthew Sperzel
Style White Shorts With a Printed Top and Red Heels
Image Source: Getty / Christian Vierig
Style a Silk Cami With Denim Shorts and Orange Heels
Image Source: Getty / Christian Vierig
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Pair Your Bermuda Shorts With a Sleek White Blazer and Bedazzled Heels
Image Source: Getty / Edward Berthelot
Style White Shorts With a Belted Blazer, Sunglasses, and Beige Heels
Image Source: Getty / Timur Emek
Style Bermuda Shorts With a Bucket Hat and PVC Heels
Image Source: Getty / Christian Vierig
Style White Shorts With an Animal-Print Top and White Heels
Image Source: Getty / Christian Vierig
Pair Biker Shorts With a White Sweatshirt and Red Heels
Image Source: Getty / Christian Vierig
Style Beige Shorts With a Belted Blazer and Brown Heels
Image Source: Getty / Matthew Sperzel
Style White Heels With Tie-Dye Shorts and a Matching Shirt
Image Source: Getty / Christian Vierig
Style Square-Toe Heels With a Blazer and Baggy Denim Shorts
Image Source: Getty / Claudio Lavenia
Style a Two-Tone Top With Black Shorts and Simple Heels
Image Source: Getty / Kirstin Sinclair
Pair Your Bikers Shorts With a Blazer and Red Heels
Image Source: Getty / Christian Vierig
Style Leather Shorts With a Striped Shirt and Red Heels
Image Source: Getty / Christian Vierig
Style Your Denim Shorts With a Button-Down Blouse, Trench Coat, and Lace-Up Heels
Image Source: Getty / Christian Vierig
Style Black Bermuda Shorts With a Pink Jacket and Ankle-Strap Heels
Image Source: Getty / Jeremy Moeller
Style Yellow Shorts With White Heels and a Purple Top
Image Source: Getty / Jeremy Moeller
Style Jeweled Heels With Baggy Shorts and a Plaid Blazer
Image Source: Getty / Christian Vierig
Style Denim Shorts With a Checkered Blazer and Black Heels
Image Source: Getty / Matthew Sperzel
Style Black Shorts With a Bodysuit, Oversize Blazer, and Strappy Black Heels
Image Source: Getty / Kirstin Sinclair
Style White Shorts With Strappy Black Heels and a Yellow Top
Image Source: Getty / Jeremy Moeller
Style a Striped Button-Down Over Shorts and Jeweled Heels
Image Source: Getty / Kirstin Sinclair
Style Light-Wash Shorts With a Plaid Shirt and Ankle-Strap Heels
Image Source: Getty / Christian Vierig
Style White Shorts With a Colourful Sweater and Orange Heels
Image Source: Getty / Kirstin Sinclair
Style Black Shorts With a Brown Jacket, Orange Vest, and Black Heels
Image Source: Getty / Edward Berthelot