Do High Heels Look Good with Shorts?

“The onset of summer often leaves us pondering whether heels can, in fact, be paired with those leg-baring summer shorts. The short answer is: absolutely!” –Ask a Stylist.

I didn’t expect such an emphatic “Yes” from Stick Fix’s “Ask a Stylist” expert concerning wearing high heels with shorts. Normally I wouldn’t recommend this. That’s because I don’t wear shorts for formal occasions unless they flare out like a skirt to at least mid-thigh.

Maybe I changed my mind after all, however. I did find some ways that high heels may look good with shorts that I hadn’t thought of until now. 

FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point. Also, assume links that take you off the site are affiliate links such as links to Amazon. this means we may earn a commission if you buy something.

Daring Ways to Wear Shorts With Heels

1. With Cuttoff Jeans

No daisy dukes for me personally – too large of thighs, but I do like the idea of a cheetah print close-toed pump or a strapped open-toed sandal for those of you who look good in short, cutoff jeans. The leopard or tiger variations have a similar effect, in that they draw attention to your feet and your legs.

Wearing animal print patterns with cutoff shorts especially looks chique if paired with a print shirt of the same and a denim jacket or oversized shirt. By the way, adding leopard print to your wardrobe doesn’t have to be “skin-tight and, for lack of a better word, slutty,” a stereotype refuted by Cosmopolitan magazine.

2. With Print Short Jumpsuits

I’ve seen wedged heels with pastel beach jumpsuits that have starfish, seashells, seahorses or other ocean life symbols printed on them. However, I thought a Matisse or Ave blocked platform sandal would look splendid for wearing by the ocean.

I consider them a “nice change,” and they’re probably easier to walk in than wedged heels. You’d wear them near the beach but not necessarily right “on” the sand or in the water.

3. With a Bright, Multi-Colored Romper

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I found an entire outfit idea that I like. Notice the uniqueness of the shoe upper you see in the photo. Chances of finding the exact shoe may not happen, but it gives you an idea of how a plain pump or another closed-toe heel that has just a little accent, ornament or color splash on the “hood” could dress up a comfortable outfit.

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“Whether it’s with a pair of daisy dukes or silky, PJ-inspired tap pants, high heels are always a great addition,” says Hollywood life in 2022.

This fashion publication features Taylor Swift in wearing a gladiator heel from 2019 that I’ve never seen before that I think complements a rather loud, multi-colored romper well.

Bravo, I say, and this probably has made me change my mind about wearing heels with shorts for good. Although, I usually wear solid colors these days. The orange gladiator heel I found doesn’t do the original justice, but I like it, and it’s the closest I could find so far.

4. With Leather (or Faux Fabric) Short Jumpsuits

The first celebrity photo I saw had basic black, minimalistic strapped shoes. However, I’m tired of recommending the same heeled sandal for every outfit. Therefore, I decided why not this strapped wedged heel?

Besides, if you’re doing any amount of walking in your heels, these probably would provide you a bit more comfort and balance. I wouldn’t wear them on an offroad trail but would stroll through a city park path.

The fabric has a surface texture that may match with any leatherlike or suede jumper.  I’ve seen similar with leather or leather-like uppers, so you have options.

5. With Creased Dress Shorts

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Jennifer Garner had a rather conservative dress short outfit on in 2018. It featured what appears to me as a black shirt with navy blue creased shorts.

She wore a basic, black closed-toed heel with them. Hers look more like strapped pumps, but I chose ones with a chunky heel and thicker ankle strap that both an ankle and upper shoe buckle.

Any closed-toed pump or strapped sandal would look just fine with this outfit though. I think it’s even dressy enough for some office environments that allows its employees to wear cooler bottoms in the summer.

6. With White Shorts

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I may be overselling heels with white shorts a bit too much. It’s mostly to convince myself more than you that this is a good idea. White shorts are hard to pull off to begin with, and then to add heels?

Well, apparently, Kim Kardashian pulled off a pair of sandals that have a netted upper she wore with white shorts. She paired these two items with a low-cut, V-neck top. You might not find the original outfit shoes, however. I at least wanted you to imagine what the upper looked like on Kim’s shoes.

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Not finding an exact celebrity match forced me to come up with my own ideas. I just found what I think maybe the most fun netted heel I’ve ever seen.

It has some print on the upper’s rim, which I think can make (in my opinion) the boring white stand out if you also find a print top with similar colors. I couldn’t decide, however, between those and the next pair I found.

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Normally, I don’t wear pump or stiletto heels because I’m not gifted with poise. However, the refined, netted upper of these open-toed shoes caught my attention. An ankle strap finishes them off, and you could pair them with just about any dress short or romper outfit that you want.

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Just for fun, I also found a pair in bright green. Similar ones come in bright yellow, orange, red and other light and dark shades. Just when I ran out of shoe ideas, I now understand why “Carrie Bradshaw” from Sex and the City loved footwear so much.

With seeing all the outfits Sarah Jessica Parker wore in that show, I’m surprised now that I was so against wearing heels with shorts. Okay, so SJP normally wore them with “ballet tutu” styled skirts, but those skirts measure approximately the same length as most shorts do, so why not with white shorts too?