The comfort fallacy
Henry's Access, centaur haunches, footwear wizards & more
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Our brand-new 2025 G.I.F.T.S. List is here.
2025 was The Jacket’s Year — the 21 best are here.
If you haven’t seen our newly updated list of The 50 Slappiest Clothing Shops Across the Spyplane Universe, we’ve been officially recognized by the paper of record as Cool Store Authorities:
The other day, the New York Times got in touch and asked me and Erin to name 4 excellent shops in the U.S., as part of a big package they just published celebrating good small American clothing stores. Those picks are above.
Since we are Global Citizens, though, you’ll see that, in our own 50 shops roundup, there are many great U.S. shops represented, but the No. 1 store on the planet is actually in another country…
I (Jonah) want to spark off today’s Plane with some thoughts about what I’ve come to regard as “The Comfort <~> Coolness Fallacy.”
A piece of style advice you encounter so often it’s become axiomatic is that if you aren’t comfortable wearing something, you won’t look good in it. This makes abundant sense — to a point. If you see someone, e.g., tottering around in stack-heel boots whose physics overwhelm them, for instance, it is not a swaggy sight. Ditto someone wearing a bold print with palpable, unconfident unease. “This person looks uncomfortable,” you say to yourself, “ipso facto they look uncool.”
The logic is undeniable. Where things get fallacious, however, is when people interpret this to imply the opposite, too, i.e., “If you feel comfortable wearing something, you will ipso facto look cool in it.”
That is false. To be clear, I’m not doing a “schlubs who wear sweatpants in public look depressing” thing here. People who say things like that have an obvious, low-hanging point, but also they tend to sound like scolds, whereas Spyplane is too big-brained, non-doctrinaire and chill to go there.
I’m thinking, instead, of more nuanced instances when the prerogatives of fit, taste and sauce require that you re-calibrate your own sense of comfort.
Case in point: I’ve long been at my most comfortable when I sag my pants a bit. And many pants look great sagged. But depending on the cut and weight of the pants in question, sagging can, in some circumstances, produce an unfortunate silhouette where the backside bulges out along a horizontal axis, creating a clot of artificial volume in the upper block that resembles Centaur Haunches.
I hate when my pants do this. There are hot Centaurs, no doubt. But I do not like the Dumpy Centaur look on myself.
I have a fantastic pair of straight-leg, raw-denim Henry’s jeans, patterned to fit like slightly bigger Levi’s 550, pictured above. Thanks to the way the cut interacts with the weight of the denim and my hips, these jeans do not want to be sagged on me — and if I do sag them, the Centaur effect is clear. I need to hoist them up, in a way where I initially feel less comfortable but definitively look better.
I’m using myself as an example here on some “let he who is without sin throw the first stone” s--t. But friends, I’m warning you, I’ve seen enough Centaur Haunches not working on other people, IRL and in fit pics, to know that this is a widespread peril that can befall all manner of trousers.
I’m not arguing that you should simply force yourself to endure discomfort & suffer in the name of swag. Quite the contrary, once you interrogate your sense of discomfort vis a vis the prerogatives of a certain garment, it can create a virtuous circle: I feel more comfortable in the sagged jeans at first, but knowing I look better with them pulled up makes me more comfortable.
I just had to push a bit beyond my comfort zone to get there. ♻️
Speaking of great pieces from Henry’s —
Keith Henry is not only an extremely funny dude and low-key big sweetie. He’s also one of our favorite clothesmakers out.
A former skate photographer turned self-taught clothesmaker, he designs and then cuts & sews (virtually) every Henry’s garment himself at his studio in Toronto, riffing on vintage workwear styles with beautiful fabrics. I interviewed him a couple years ago here.
Henry’s releases are extremely limited, as a function of his one-man operation, and drops tend to sell out extremely quickly. So today we’re psyched and honored to offer Classified-Tier Spyfriends exclusive access to his newest capsule, which consists of 3 pieces...
The Swoop Jacket, cut from heavyweight olive brushed Japanese cotton moleskin, with contrast stitching, bar tacks, and lightly sanded silver donut buttons.
The Swoop Pocket Trouser, a classic Henry’s piece he hasn’t made in a minute, done here in the same heavy Japanese moleskin as the jacket but black, with tonal stitching, bar tacks, and densely woven weathercloth pocket bags.
The first checked button-up Keith’s ever done: the Spade Shirt in a midweight yarn-dyed cotton poplin “with a bit of crunch to it and a slightly brushed hand,” he says, finished with corozo buttons.
To access the capsule 🪡🪡🪡 use the Classified-Tier portal & passcode at the bottom of today’s sletter 🪡🪡🪡.
Meanwhile —
Mamma mia, when these people make shoes, they don’t miss: