In The Name of Logic, Explain My Love For Big Boots With Shorts

Forgive me for stating the obvious, but shorts are for summer and big chunky boots are for winter — right? That’s what’s been hardwired into my brain from a young age, but I’m starting to doubt myself.

When you’ve got the likes of Tyler, The Creator cutting around in a puffer jacket paired with shorts, it makes you doubt everything you knew about seasonal dressing.

It’s difficult to explain in words why I’m starting to look at the pairing in a different light — maybe it’s as simple as a pair of boots being more interesting to look at than empty, undressed shins. Or maybe it’s that it lets the tops of a pair of boots, normally covered by trousers, finally get some shine.

But look at Pedro Pascal’s outfit from the 2023 Met Gala and it’s hard not to admit that there’s something about boots and shorts that just works. The actor, whose style has been a sartorial highlight of 2023 so far, even managed to make the unconventional combination look the part together with a suit and it became a highlight of the Gala’s ever-entertaining red carpet.

And it’s not just Pascal, you have A$AP Rocky going full New York in a pair of Jorts and Timberland Boots, Evan Mock exploring fashion week in above-the-knee shorts and military-style boots, and Amelia Gray Hamlin leaving only a little bit of knee on show between her biker-style boots and baggy workwear shorts.

In womenswear, it’s been a relatively normal thing to do, pairing heeled boots with a skirt or shorts isn’t really considered anything worthy of comment but that hasn’t been the case in menswear. And it’s good to see the styling appreciated across the board.

The more I see it, the more inclined I am to take the plunge and add a pair of long-shafted leather boots to my spring/summer wardrobe. And the runway has been endorsing this frivolous wish.

During the SS24 shows, it felt like there were boots and shorts at every turn, from the street style to the most spoken-about collections. Pharrell’s Louis Vuitton debut was littered with examples as were collections from the likes of KENZO, Undercover, and GmbH — to name just a few.

Take a look at some of our favorite shorts and boots pairings below, and decide whether you would like to join the logic-defying fun. Or, of course, you can just stick to pairing sneakers and shorts.

Scroll down for our favorite shorts and boots combinations

The talk of the hiking trail

Shorts and boots are for everyone and that includes all the gorp lovers. Focusing on function, we’ve put together cargo shorts with Timberland’s hiking boots, made in collaboration with Nina Chanel.

Hot fuzz

Both featuring cozy, fuzzy fabrics, these shorts and boots look like they’re made for each other. If you’re not willing to ditch shorts this early into fall, this pairing will keep you cozy.

Margiela madman

For a full western look, the only thing to pair cowboy-style boots with is raw-hem denim shorts. Fashion’s cowboy obsession isn’t slowing down and we are more than happy to feed into it with designs from Maison Margiela.

No leg on show

While Jacquemus’ shorts fall just below the knee, Kiko Kostadinov’s lace-up boots are knee-high — meaning they’ll meet in the middle of your leg. For those who don’t like showing their legs, we’ve got you.

An ode to Southern America

Although neither Kapital nor Dr. Martens are American brands, the pairing of these boots and patchworked denim shorts would look most at home in the American South. That is, in large part, thanks to all the graphics on the shorts.

Monochrome minimalism

If you’re still feeling a bit unsure about making shorts and boots work, you can’t go wrong when keeping things simple in black and white.

Something that shouldn’t work

Beach shorts and polar boots? It doesn’t get much more juxtaposing than that. However, since both the boots and shorts are made from nylon, they work together.

Tiny shorts, huge boots

On a scale of UGG-ly to UGG-cellent, Telfar’s re-interpretation of the classic brown sheepskin boot is up there with the best. We’ve paired the big boots with some contrastingly tiny denim shorts.

Fashion-fied Workwear

Made in collaboration with boot manufacturer Bogs, these shoes are pretty much ready for anything. They come with waterproof 5MM Neo-Tech-insulated bonded jersey, DuraFresh odor-resistance, and Bogs Max-Wick moisture-wicking technology.

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