This Summer Outfit "Mistake" Is Cool Again—8 Looks to Prove It


Before we dive in, I want to put it out there that I think fashion "rules" are silly and outdated. We're all past the point of letting anyone else's opinion dictate what we wear or don't wear because, well, style is so personal. That being said, I'm sure you can think of a few fashion mistakes you've been warned of before, whether it be wearing white past Labor Day or mixing gold and silver jewelry. One arbitrary style mistake that has managed to stick with me for years is wearing shorts, especially denim shorts, with boots.

I can't tell you where I first read this tidbit, but it's remained in the recesses of my memory for years now, and I think it's finally time that we do away with it for good. I'm not alone here. Fashion people are styling their shorts with tall and mid-calf boots more than ever this summer, and they're putting the final nail in the coffin for this outfit "mistake." Ahead, see all the cool shorts-with-boots outfits that are popping off on the 'gram right now, and get inspired to dive into the combo yourself.


(Image credit: @dualipa)

When Dua Lipa posted this look to her Instagram, I immediately took note of the Daisy Dukes–meets-fashion details like the cutoff shorts, tall Western boots, and, ahem, gingham Miu Miu jacket.

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(Image credit: @cassdimicco)

I'm into this low-key summer vibe with one of the closet staples everyone's loving, a relaxed button-down shirt. The addition of Western boots makes the simple formula really pop.

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(Image credit: @sofiamcoelho)

Your favorite knee boots from the fall and winter deserve some airtime in the summer, too. Style them with relaxed shorts for a cool take.

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(Image credit: @chanelmckinsie)

Denim shorts often come off as casual, but these sleek knee boots and this all-black palette look so elevated.

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(Image credit: @goodwoodx)

I realize that suggesting you wear cowboy boots in the heat of summer is a radical thought, but you can't look at this outfit and tell me a different pair of shoes would look better. 

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(Image credit: @ashley_moore_)

Western boots are an unexpected way to jazz up a casual jean-shorts-and-graphic-tee combo.

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(Image credit: @devonleecarlson)

If everyone's favorite It girl Devon Carlson is getting behind the outfit idea, you know it's only a matter of time until more people follow suit.

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(Image credit: @devapollon)

While traditional Western boots in neutral tones are pretty timeless, funky color combinations are quickly becoming a favored style among fashion people, and this fun-loving shorts outfit is proof.

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Next up, see the 7 summer items I'm tossing for a wardrobe glow-up and 7 I'm adding.


Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.