The Shoes We Never Wear With Shorts

last updated 1 May 2018

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).

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

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"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

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"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

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"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

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"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

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"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

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"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

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"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

BALLET FLATS

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

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

Shop Ballet Flats:

Topshop

Violet Satin Ballet Shoes

Repetto

Checked Ballerinas

OLD-SCHOOL SNEAKERS

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

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Who: Karlie Kloss

Shop Old-School Sneakers:

Adidas

Gazelle Sneakers

Converse

Low Top All Stars in Natural

KITTEN HEELS

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.

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On Leandra Medine: Reformation top.

Shop Kitten Heels:

Maryam Nassir Zadeh

Whiskey Suede Andrea Mules

Zara

Silver-Toned Leather Mules

ESPADRILLES

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.

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

Shop Espadrilles:

Castañer

Kitty Striped Canvas Espadrilles

& Other Stories

Leather And Suede Espadrilles

FLAT SANDALS

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

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

Shop Flat Sandals:

Who What Wear

Emma Buckle Slide Sandals

Alberta Ferretti

Mia Mule Pool Sliders

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

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Style Tips

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.