The Shoes That Look Best With Shorts (and 5 Styles That Are Meh)

If you were to rattle off the summer staples in your wardrobe, there’s a strong chance that shorts would be toward the top of the list. Well, it makes sense given the practical and stylish nature of the essential. On that note, we thought we’d bring you a range of standout shorts silhouettes if you’re looking to add a fresh pair to your rotation. But we’re actually taking it one step further and showcasing the shoes that look best with shorts. Alternatively, we also wanted to highlight the shoe silhouettes we’re not as into with shorts at the moment given their somewhat outdated nature. Of course, remember that you should really just wear what you love and what you’re most comfortable in.

Keep scrolling to check out testimonials from the team about the shoes to wear with shorts this season and those that you might consider skipping. You’ll also find inspiration imagery from various style setters that showcase the best shoes and shorts.

Into: Slide Sandals
Not as Into: Ankle Boots

How to wear sandals and shorts



"Shorts are a mainstay in my summer wardrobe and a key piece to wear on vacation, so I tend to pair them with other suitcase essentials like flat slides. While I think there are some directional ways to pair shorts with knee-high boots this season, I would skip ankle boots." — Kristen Nichols, senior editor

This relaxed fit is a must for comfortable summer style. 

A more streamline version of the fisherman sandal. 

Tailored shorts can be dressed up or down easily. 

Polish off your shorts outfit with smart mules. 

A great pair of denim shorts can be relied on year after year. 

Into: Kitten Heels
Not as Into: Pumps

"I think sleek kitten-heel sandals are a great companion to tailored shorts. They will elongate your legs a little, and the low height maintains an ease that feels right paired with casual shorts. Pumps on the other hand can feel a bit off with shorts. It can work with the right pairing, but it's less of a natural fit." — Kat Collings, editor in chief

The flared kitten heel makes these easier to walk in. 

Longline shorts keep coming back each summer, and this relaxed style has me convinced to buy. 

Wear relaxed with a tee, or elevate with a shirt for a more tailored look. 

Sitting just below the knee, these Bottega shorts are the perfect silhouette for kitten heels. 

Into: Loafers
Not as Into: Ankle-Tie Shoes

"I'm very particular with how I style shorts, and I won't wear them with just anything. One shoe style I'll always avoid with shorts is anything with an ankle tie detail since they cut off my legs in an awkward way. On the other hand, I'm intrigued by the combination of loafers with denim shorts—the classic flats add polish to an otherwise super casual summer staple in a such a cool way." — Anna LaPlaca, editor

These black denim shorts are tailored with pleat details but retain their relaxed form for an uber cool style. 

These monochromatic loafers will look just as good with jeans or dresses. 

In airy linen, these will be a go-to piece for the warmest days. 

These will look so good with denim shorts (and there's some coming up next!).

A loose fitting cut, and bermuda style combine for the perfect off-duty denim shorts. 

Into: Sneakers
Not as Into: Wedge Espadrilles

"I live in the South, so I live in shorts during the hot and humid summer. When it comes to the shoes I don't wear with them, a style I avoid is wedge espadrilles with shorts. It's a pretty dated look in my opinion. I usually stick to flats and sneakers—classic Converse always work." — Allyson Payer, senior editor

This versatile pair will look great with every shoe style we're into. 

Fashion followers everywhere love Veja. 

Another iconic trainer that fails to go out of style. 

The ultimate shorts for 501 lovers. 

Into: Flatform Sandals or Elevated Thong Sandals
Not as Into: Standard Flip-Flops

The best shoes to wear with shorts for women



"I have a love-hate relationship with shorts. Most pairs have a way of making my legs look—well—shorter, and at just under 5'4", that's the kind of thing I like to avoid at all costs. The chunky, flatform sandal trend is truly a blessing, as it's the only sandal style that solves my short-girl-wearing-shorts dilemma. Everything from strappy sandals to elevated (in more ways than one) thong sandals is on my radar. However, I will be avoiding traditional flat flip-flops when styling my shorts looks this summer." — Michaela Bushkin, senior fashion editor, branded content

Wear dressed up or dressed down. Personally, I'm styling with the matching shirt. 

Thankfully, this cult piece has been restocked. Get them while you can. 

Rely on sporty shorts for easy outfits for running errands. 

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