The Shoes We Never Wear With Shorts

Shorts are undoubtedly a warm-weather staple, but truth be told, we can't think of many articles of clothing that are quite as tricky to wear as our beloved shorts. The reason? Simply put, they're short. So unlike something that doesn't expose quite as much leg, you can't just wear any type of shoe with them, or you run the risk of your outfit looking over-the-top "sexy" or them making your legs look shorter. But that doesn't mean that there aren't plenty of options when it comes to what shoes to wear with shorts.

Enter: Your shorts-loving team of Who What Wear editors. Over the years, we've tried (and skipped, in some cases) every combination under the sun, eventually coming to the conclusion that there are certain shoe styles that we'll never wear with shorts. Alternatively, there are certain shoes that we wear with shorts on repeat (and you'll probably want to, too, once you see how chic they are).

Because summer is coming, keep scrolling to find out which shoes Who What Wear editors never wear with shorts (and shop five shoe styles that are perfect with shorts).

best shoes to wear with shorts

"I wouldn't wear short shorts with a high wedge. The shorter the shorts, the lower the heel should be." — Kat Collings


See how Kat would wear them with kitten heels:

On Leandra Medine: Reformation top

This one may seem surprising, but the low heel of an on-trend kitten-heeled shoe is a great option when you want a little height but (obviously) want to look cool and not over-the-top.

Shop Kitten Heels:

"Pointed-toe heels are probably the last shoes I'd wear with a pair of shorts. Instead, I typically go for a comfortable block heel or simple slide." — Michelle Scanga


See how Michelle would wear them with slides:

Kiernan Shipka wearing shorts


Splash News 

On Kiernan Shipka: Chanel sandals

We'll be wearing sandals with just about everything this summer, including shorts. Our current favorites? Effortless slides, without a doubt.

"High-top sneakers! I'm five-foot-two, so high-tops and shorts are a recipe for looking stumpy for me. I prefer something more delicate, like flats or sandals, or something with a little height, like ankle boots." — Nicole Akhtarzad


See how Nicole would wear them with espadrilles:

Alessandra Ambrosio wearing shorts



On Alessandra Ambrosio: Re/Done Levi's High Rise Shorts ($175); Saint Laurent bag; Valentino shoes

Espadrilles, the unofficial shoes of summer, are a no-brainer when it comes to shorts. Our advice? Stick to flat espadrilles instead of wedge-heeled pairs.

Shop Espadrilles:

"I'm not fond of wearing shorts with athletic sneakers. It makes me feeling like I'm going hiking or camping (in a bad way). On the other hand, I love wearing them with more retro sneaker styles, like Adidas Gazelles or Converse Chuck Taylors." — Allyson Payer


See how Allyson would wear them with old-school sneakers:

Karlie Kloss wearing shorts



Who: Karlie Kloss

Skip high-tops and athletic sneakers, and instead opt for a pair of retro sneakers for a pairing that fashion girls love.

Shop Old-School Sneakers:

Available in sizes 36 to 41.

"I always avoid wearing heels with shorts (unless they're short block heels). I'm five-foot-10, and all of my shorts are quite short, so it's a bit ambitious to try to wear them with heels. Plus, the shorts I own are all very casual, so I wouldn't want to wear them with dressier shoes." — Erin Fitzpatrick


See how Erin would wear them with ballet flats:

Alexa Chung wearing shorts


Splash News 

On Alexa Chung: Saint Laurent sunglasses; Longchamp clutch; Repetto Cendrillon Ballet Flat ($295)

A gamine pair of ballet flats will always be a chic, polished choice of footwear with just about anything, including shorts.

Shop Ballet Flats:
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