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Every Pair Of Shorts I’m Actually Wearing This Summer

Every Pair Of Shorts I’m Actually Wearing This Summer

The 13 best shorts I own, and which will make getting through the season a breeze.

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JAKE WOOLF
Jul 03, 2025
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Every Pair Of Shorts I’m Actually Wearing This Summer
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At this exact moment, as I stare down the looming arrival of fall collections at retailers everywhere, I’m making a conscious decision to live in the now. Yes, the fashion calendar says it’s almost time for coats and chunky knits. But outside? It’s very much still summer. It’s hot. And I’m wearing shorts.

So let’s forget about layers for a moment. Instead, kick back, relax, and let’s talk shorts. But first, a little context. Trend-wise, in 2025 the stranglehold that 5” inseams had on menswear for the last few years has officially loosened. Instead, in 2025, big shorts reign supreme. Now, I admit that this has been great for me, a noted big thigh haver. I appreciate the comfortability (and lack of accidental upper leg exposure) that comes with the extra length and width. But don’t be alarmed—a lot of the pairs in my arsenal still hit above the knee, and nothing I’m slipping into this season is approaching “Kevin Smith at the gas station” length. (Okay, there’s one pleated nylon pair that graze my shins, but a) those rock and b) the rest are, I assure you, well within reason.)

Normally this is the part where I’d say I scoured the market to compile a list of all of the best shorts on the market. But today I’m keeping it personal. As such, here are the 13 pairs that are actually in my rotation this season. There are jorts. There are pleated, preppy styles made by the GOAT. There are some versatile, water-resistant staples that pull double duty. And there’s even my favorite pair of gym shorts that I break out as I frantically attempt to get my summer body into form. (Thus far the results on that front have been mixed, though that’s no fault of the shorts themselves.) Point is, not only do I think all of these shorts are great, but can personally vouch for each. So let’s get to it, and as always, enjoy!

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This newsletter is ENTIRELY funded by subscriptions. I don’t use affiliate links, and all of these products are things I’ve endorsed because I actually like them—though in some cases I did not pay for them. Point is, your subscriptions are both extremely cool and very much appreciated. Thank you!

The 13 Pairs Of Shorts I’m Actually Wearing This Summer

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