The year jackets rocked again
The 21 best of 2025: natural-dyed, waterproof, cropped, on their “plump dumpling” flow & more
Our brand-new 2025 G.I.F.T.S. List is here.
Mach 3+ city intel for traveling the entire planet is here.
Enjoy our new, definitive guide to the Best Japanese Clothesmakers Out.
🪡🪡🪡 In this coming Thursday’s Plane, we’re proud to offer Classified-Tier Early Access to a new capsule of clothes from Henry’s: an olive Japanese moleskin Swoop jacket, generously cut black moleskin trousers, and Keith’s first-ever checked button-up. Like all Henry’s drops, stock will be limited, because he made everything himself. The newsletter will go out at 7 a.m. PT / 10 a.m. ET
A few years ago, after extensive research, we published a graph ranking the most crucial parts of an outfit in terms of looking cool, in ascending order of importance. These were:
1. Shirt, 2. Jacket, 3. Shoes, 4. Pants, and 5. How Your Pants Meet Your Shoes.
I (Jonah) have written a lot about the high-risk, high-reward, vexatious power of pants, so I don’t need to dig back into that topic now, beyond noting that our pants-weighted findings remain true.
But shirts and jackets — while less important than the Footwear-Ankle-Pant Interface when it comes to a Holistically Considered Sauce Gestalt — are, of course, far from unimportant. And the other day, I realized that over the past ~12 months I’ve thought with more excitement about jackets than any other garment. Many of our favorite designers did their best work in the form of jackets. The saucely detail I was likeliest to clock first when encountering well-dressed people was — you guessed it — which jacket they were rocking.
Add it all up, and the truth is undeniable: this year, pants and shoes took a backseat to the outer layer. 2025 was The Jacket’s Year.
What accounts for this? Part of it has to do with the normal way that trends, like all historical contingencies, can ebb, flow and shift even as overarching verities stand intact. The Beatles remain the most important rock band (for the sake of argument) even in a year when Mac DeMarco put out the best rock record.
But I think there’s a deeper psychological dynamic at play, too. These days we feel so much uncertainty in our lives, about so many different things, that something finally had to give.
For the Cool Clothes Appreciator, that something was pants. After several years of stress, paroxysm and tectonic change as relates to our understanding of Good Pants, we finally pushed back from the table, unbuckled our belts, let out a deep breath, and gave the fraught business of worrying about our trousers a rest. Cropped, pooling, cuffed, unfurled, straight-leg, carrot-leg, pleated, flat-front, voluminous, fitted, Hedi-grade skinny — all were theoretically acceptable. We eased the tolerances, wore the same pants we wore last year, stopped Policing Our Pants with the same intensity we’d brought to bear on them circa 2021-2024.
Instead? We let ourselves nestle into the much more relaxed, much more forgiving, far lower-stakes, downright escapist pleasures of the jacket.
Jackets don’t demand as much of us as pants do. The most straightforward way to illustrate this is to imagine both garments in an e-comm context. Between a jacket and pants, which are you likelier to see in a .jpeg and, absent any further information besides measurements, smash the cop with a strong level of confidence re: how it will look on you? It’s obviously the jacket ~9 times out of 10. And while the dopest possible jacket will never match the dopest possible pants as far as Holistic Outfit Enswaggenment, a sick jacket is a major blessing all the same.
All of which brings us to today’s Plane, where I’m saluting my favorite jackets of 2025.
I styled & photographed 10 of them for you in the form of “Flung Fits” — Blackbird Spyplane’s delightful solution to the problem of the Boring Fit Pic.
These are numbered but unranked. Most are technically men’s, but that doesn’t matter to Erin when she’s rummaging through my closet for something she’s going to steal and look cooler wearing than I do, and there’s no reason it should matter to you, either.
Let’s get to it —
