A Guide to Pairing Your Shorts With Heels

A Guide to Pairing Your Shorts With Heels

At first thought, wearing shorts with heels might not seem like a match made in heaven but we beg to differ. Shorts paired with heels is one of the most fun and chic ways to show off those stems while looking and feeling divine. In all fairness, this styling combo was seen as unconventional for a long time, but times have changed! Shorts paired with heels can be cute, stylish, and sassy.

We've compiled some of our styling tips on how to best wear shorts with heels this summer and even into the early fall. The key to wearing heels with shorts is to be sure that the entire outfit strikes a balance among all the elements without bringing too much attention to the heels or the shorts.

Denim Shorts

Jean shorts are some of the most beloved of the women’s shorts world. Depending on how you style them, you can wear them with a wide variety of heels. Wear a cute pair of denim shorts with a pair of mules, a summery blouse, and a leather shoulder bag for a cute casual chic look.

Denim shorts offer a kind of rugged edge to any outfit. A perfect late summer or early fall outfit is to wear some high-waisted jean shorts with a flannel shirt and some block-heeled calf-high boots. This fun western-inspired look is perfect for coffee dates, family outings, or fall-inspired activities like apple picking or pumpkin patch exploring. If the flannel is too much rustic in one outfit for you, opt instead for a nice long-sleeved top with a casual blazer.

Bermuda Shorts

Women’s Bermuda shorts are fun, flattering, and fashionable. Wear Bermuda shorts with a pair of kitten heels and a blouse for a sophisticated and sharp look that is even suitable for some professional environments. Kitten heels offer a modest height, while Bermuda shorts offer more leg coverage, making this pairing perfect for those who want to wear heels with shorts, but not necessarily draw too much attention to themselves. It’s perfect to wear to a barbeque or outdoor gathering or even while on vacation. If kitten heels aren’t quite your thing, then instead wear Bermuda shorts with block-heeled mules for a more casual overtone.

Flowy Shorts

Loose and flowy shorts are a summery favorite that can easily be dressed up or dressed down. It’s probably no secret that a great way to dress up these beauties is with the perfect pair of heels. Summery and down-to-earth, wedges make a wonderful match with loose and comfortable shorts. We love wedges paired with linen, silk, or satin shorts. This relaxed look is perfect for just about any occasion. Dress up with a blouse and blazer or down with your favorite women’s T-shirt. The wedges have the added perk of being decidedly more comfortable than most heels, making this one of our favorite relaxed and yet no-less-stunning shorts-and-heels combos.


Onesies, rompers, and jumpsuits pair spectacularly with heels. Wear a shorts-style onesie with a pair of booties for an easy go-to outfit that still looks effortlessly fashionable. Wear a darker romper with brown leather booties and a denim or leather jacket for a great look that is also perfect for transitioning into fall. For spring and summer looks, opt instead for brighter colors and floral prints. Cream-colored suede zip booties look fabulous with a silky floral romper and a linen jacket for a stunning and sophisticated summery ensemble.

Khaki Shorts

This look is the perfect casual chic outfit. Wear women’s khaki shorts with a white button-up blouse and your favorite pair of heels. We recommend heels that have a neutral color or tone to match the creaminess of the rest of the outfit. Wear strappy stilettos or your suede mules—this outfit is going to look amazing either way. Perfect to dress down, easy to dress up, this simple combo is timeless and classy.

High-Waisted Shorts

High-waisted shorts are classy and sassy with a stylish retro twist. Wear high-waisted shorts with block-heeled booties or ankle-strap heels. Wear with a loose and flowy top or women’s linen shirt for summer months, and silk or satin shirts for cooler months. You will look sweet and sophisticated with this outfit.

Cropped Shorts

This look is not for the faint of heart, but it is perfect for nights out and showing off those lovely legs. Wear a pair of shorts with a shorter hemline and your favorite pair of statement stilettos. This look will get people turning heads when you walk into the room. Wear with a sharp blazer with a longer hemline and a belt for an incredible ensemble. Go the extra mile and throw on that bold red lipstick, too. You’re going to be turning heads anyway, so enjoy being tastefully extra and absolutely fabulous.

Now that we’ve debunked myths about heels and shorts being taboo together, we hope you’ll go on to explore this fun and chic way to combine some of our favorite wardrobe pieces.


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