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we also wanted to highlight the shoe silhouettes we’re not as into with shorts at the moment given their somewhat outdated nature.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

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

"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

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

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

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