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 shoe style with them, or you run the risk of your outfit looking over-the-top "sexy" or them making your legs look shorter.

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.

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).

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

"I'm not a fan of pairing stilettos and shorts. The result just feels a little off-kilter, since super-high heels are a night-out pick for me, while shorts are a more casual choice." — Aemilia Madden

"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

"High-top trainers! 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

"I retired my flip-flops years ago, so I don't have a single pair in my wardrobe—and I wouldn't bring them back for a pair of denim shorts. In place of them, I wear comfortable but stylish slides. All you need to add is a cool statement top." — Kristen Nichols

"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

"I'm not fond of wearing shorts with athletic trainers. 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

"I would never wear flat Chelsea boots with shorts. I personally feel like that style (when worn with shorts) cuts off your legs at an unflattering place. In addition, the fact that there is no heel height means your legs aren't getting elongated in any way, which is something I think your shoes should do for you when you're wearing shorts." — Lauren Eggertsen

Pairings We Recommend


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

Best shoes to wear with shorts: Alexa Chung


Splash News 

On Alexa Chung: Saint Laurent California Sunglasses (£287); Longchamp clutch; Repetto Cendrillon Ballet Flat (£180).


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

Best shoes to wear with shorts: Karlie Kloss



Who: Karlie Kloss


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.

On Leandra Medine: Reformation top.


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.

Best shoes to wear with shorts: Alessandra Ambrosio



On Alessandra Ambrosio: Re/Done Levi's High Rise Shorts (£205); Saint Laurent bag; Valentino Rockstud Espadrilles (£525).


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

Best shoes to wear with shorts: Kiernan Shipka


Splash News 

On Kiernan Shipka: Anya Hindmarch Smiley Crossbody (£550); Chanel sandals.

Next up, find out which S/S 17 fashion trends matter the most.

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