Look, I know there are a million articles out there telling you about the “top 15 shorts every man needs” or whatever. I’m not doing that. I’m going to tell you about two pairs of shorts that have completely replaced everything else in my rotation, and I think they could do the same for you.
The Faherty All Day Shorts for when you need to look put together. And Old Navy pull-on shorts for when you just don’t.
That’s it. That’s the whole system.
The Faherty All Day Shorts Are Stupidly Versatile
I started wearing Faherty’s All Day Shorts to a cookout last summer because I wanted something that looked a little nicer than gym shorts but wouldn’t have me sweating through khaki chinos by noon. I ended up wearing them to basically every event after that.
These things have a flat front design that genuinely looks tailored, like you actually thought about getting dressed that morning. But underneath that clean look, they’re basically performance wear. The fabric is a blend of recycled polyester, organic cotton, and elastane, so they stretch, they breathe, and they dry fast if you happen to get caught in the rain or end up near a pool. They come in 5-inch, 7-inch, and 9-inch inseams, so whatever your comfort level is with showing leg, they’ve got you covered.
There’s an interior drawstring so you get a secure fit without a visible elastic waistband, plus a proper zip fly. They look like real, intentional shorts. The kind you can wear to a rooftop bar, a nice brunch, a summer wedding (casual dress code, obviously), or just out to dinner. Nobody is going to look at you and think “that guy is wearing athletic shorts pretending to be regular shorts.” They just look good.
At around $108, they’re not cheap. But I’ve found that having one pair of shorts you actually feel confident wearing to nicer stuff means you stop buying three mediocre pairs trying to split the difference. You just grab these and go.
Old Navy Pull-On Shorts Are the Unsung Heroes of Summer
Now for the other 80% of your summer. The grocery runs, the dog walks, the couch days, the “I’m just going to grab coffee” mornings. For all of that, Old Navy pull-on shorts are perfect and I will not be taking questions at this time.
They have an elastic waistband. You pull them on. They’re comfortable. They come in like a dozen colors. They cost somewhere around $20 to $30 depending on what sale Old Navy is running that week (and they are always running a sale). The fabric is soft, lightweight, and breathable enough that you don’t feel like you’re suffocating your legs in July.
Are they fancy? No. Do they need to be? Also no. They’re the shorts equivalent of your favorite old t-shirt. You throw them on without thinking and they just work. The relaxed fit gives you plenty of room to move around, and the drawstring waist means you’re never fussing with a belt or a button when you’re just trying to be comfortable.
I own like four pairs in different colors and I rotate through them all week without a second thought. When one pair gets worn out after a year or two, I just grab another one for the price of a decent lunch. No stress.
The Two-Short System
Here’s why this combination works so well. You’re not trying to make one pair of shorts do everything. That never works. You either end up overdressed at the park or underdressed at dinner. Instead, you have a clear lane for each pair.
Going somewhere where you want to look like you have your life together? Faherty All Day Shorts. Going literally anywhere else? Old Navy pull-ons.
It sounds almost too simple but that’s kind of the point. Summer is supposed to be easy. Your shorts shouldn’t require a decision tree. You should be able to look at your day, grab the right pair in three seconds, and get on with it.
I’ve tried the Lululemon shorts, the J.Crew chino shorts, the random Amazon shorts that show up in targeted ads. They’re all fine. But none of them nailed the specific thing they were supposed to do as well as these two. The Faherty shorts outclass everything in the “nice casual” category and the Old Navy pull-ons are unbeatable for everyday comfort at that price point.
So yeah. Two pairs of shorts. One for nice stuff, one for everything else. Summer solved.

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