The Best Garments of 2025
Recapping a year of copping
About two years ago, I made up my mind to remake my wardrobe.
As the pandemic faded and I returned to a real life once and for all, I found myself doing so in the clothes of another man—someone younger and less self-assured (not to mention a little bit thinner). The world had changed, and I had changed with it. Continuing to wear the same styles and silhouettes I had during the first Trump term seemed to be a denial of this fact.
I didn’t want to discard my entire image, but I did want to re-evaluate it and determine what worked, what didn’t, and why. In short, I wanted to be intentional about dressing myself, the same way I’m intentional about what records I listen to, what food I eat, and what people I consort with.
To manage this process, I spun up a spreadsheet. I couldn’t buy everything I wanted to right away, but I could catalog it. Over time, I could also track these purchases, giving me insight into how my wardrobe was and wasn’t changing. Was I over-indexed on jackets? How long had it been since I bought new socks? Was I paying too much attention to pants? The spreadsheet revealed all (including the fact that you can never pay too much attention to pants).
Now that I’m several years into this journey, I have a bit of perspective on what I’ve accomplished and where I want to go in the future—hence this exercise. In the spirit of “showing my work,” I’m including prices along with each item. Building a wardrobe necessitates spending a bit of money, but it’s less than you might think. Many of the following pieces are reliable basics I spend all day in or eBay finds that I nabbed for next-to-nothing.
Dressing well is not at all a matter of simply spending more money. Indeed, spending less on certain things allows me to spend a bit more on a few extraordinary items. Intentionality, remember?
2025 was a great year of buying and wearing clothes. These were my absolute favorites.
Vintage Ralph Lauren Harrington Jacket — $40
A simple lightweight jacket that goes with everything.
Jackets are often the trickiest element of an outfit (not to mention most expensive). Finding the right one to pair with such-and-such a look is a delicate art. I can’t explain the rules, but I know when I see it: either it works, or it doesn’t. Sometimes this is a fun puzzle to solve. Other times, I don’t want to think too hard—I just want to throw on a jacket and walk out the door. This is the jacket I can always do that in.
Cut wide and a little bit cropped, so that it slouches down and hits below my natural waist. A bit warmer in color IRL than it appears in the photo. Has an undeniable whiff of “normcore” to it, which gives it a great deal of utility. I don’t want to “dress normal,” but I also don’t want to look like I’m trying to not “dress normal.” Dig?
Casatlantic Linen Tanger Trousers — $220
Double-pleated, billowy, and deliciously high-rise, I lived in these all summer.
The linen these pants are cut from is remarkable: thick, plush, and woven in a subtle herringbone pattern. I wouldn’t call them heavy-duty—it’s still linen—but the weight of the fabric really makes you feel like you can live your life. They drape beautifully, right down to the cuffs I had my tailor install. The pants come unhemmed, allowing you to customize the length as you see fit. I went a little long on these, giving myself a nice solid break that typically expresses itself somewhere between my calf and ankle.
Elevated enough to wear for ~occasions~ but not at all fussy. I loved bumming around in these, an undershirt, and any old top layer: chambray, denim, or even more linen. Already counting down the days until I can bust them out again.
Everybody.World Boxier Tees — $40/$44
My new default tees: wide, a little bit cropped, and, at 6.5 oz, just heavy enough.
As much as I enjoy putting together a novel and exciting ensemble, the truth is that I’m at home for a computer job ~40 hours a week. I could get fully dressed up each morning, but wearing great clothes loses some of its thrill if you’re not out in the real world. This being the case, I tend to default to steady basics that can get me through a full day of computer, dog walks, resistance training, podcasting, and so on. These tees from Everybody.World do that job best.
The secret sauce is the length. Most modern tshirts are cut long so that they can be worn with low-rise trousers. This gives the wearer a tubular, sausage-like silhouette that I find deeply unappealing.
Since I wear my pants at my natural waist (just above the belly button), I can wear shorter shirts without exposing my midriff. The Everybody.World tees hit me just wear I want them to, and they’re cut with plenty of slack across the shoulders and chest for a loose, drape-y fit. Available in both short and long sleeve, and in all manner of attractive colors.
Vintage Ralph Lauren Chino Shorts — $27
Hardy shorts with wide thighs, a short inseam, and a handsome patina.
“Vintage Ralph Lauren X” is the search term that never fails. I didn’t even know I wanted these shorts until I stumbled across them in some insomniac eBay scroll session. It pays to pay attention to average prices of eBay listing. Plenty of stuff out there is listed at or above fair market price. If you know what that price is, it makes it easy to pull the trigger on a listing like this. At $27, I couldn’t afford not to.
Double pleated, with a classic 6” length. Seams and stitching faded to a nice robin’s egg blue, a few frays just starting to express themselves for a bit of character. Generously wide through the hem—an absolute necessity for me and my cyclist thighs.
Maximum Henry Braided Standard Belt — $160
A simple belt that works with jeans, suits, and anything else.
Belts can be deceptively difficult. I tend to want something functional and quiet, but not so bland as to disappear completely. I’m also looking for something made of natural materials that will look better, not worse, as it ages. No plastic “vegan leather” for me, thanks.
Maximum Henry goods check all those boxes. The belts are made to order in New York City, allowing you to dial in your exact preferences in terms of width, leather color, and hardware color. This one is 1.25” wide, deep brown, with a silver buckle. I ordered mine a few inches long so that I can knot it up at the end (and to give myself a little room to grow in the future…).
Styles will come and go, but belts are here to stay. I fully expect this one to last a lifetime.
Foxfibre®️ Crew Socks — $33/3 pack
Daily driver socks made from organic, dye-free cotton grown, spun, and knit in these United States.
For the last several years, my sock collection has been composed of two primary types of socks: the Los Angeles Apparel Unisex Sock, good for wear with sneakers and hikers; and over-the-calf dress socks that pair with loafers, bluchers, and so on. These live somewhere in between. They’re shorter and a bit thinner than the Los Angeles Apparel socks, but hardier than the dress socks. As such, they go with everything in my shoe rotation. Keens and Bedrock Mountain Clogs make a particularly nice match with the short, slack fit.
The central appeal, however, is the fabric. Sally Fox developed her namesake cotton to grow in a variety of warm, natural hues that obviate the need for dyes. In an increasingly plastic world drowning in vulgar, synthetic fabrics, it’s reassuring to walk around all day in entirely natural fibers (or almost entirely—there’s a bit of nylon woven in for a tight, elastic fit). Extra credit for the MiUSA aspect, not only from an economic angle, but also from an environmental one.
Earth\Studies ESCEP Jacket — $295
A functional, asymmetric riff on the classic fleece zip-up.
One of the more recent additions to my wardrobe, this jacket has already proved its worth. In pitch dark San Francisco mornings, I need a solid top layer I can just throw on to walk the dog and make coffee—something big, soft, and warm. Recently, I realized the Patagonia Synchilla I had relied on for years was no longer doing it for me: too thin for frigid 5:45 AM temperatures, too tight around the chest and upper arms.
The Earth\Studies ESCEP solves both problems and more. With full, rounded shoulders and generous sleeves, the jacket gives me plenty of room to maneuver. The superthick fleece is dyed an odd, compelling shade of brown that somehow, in certain lights, seems to verge on purple. It’s also finished with all sorts of functional details: double-zipper enclosure, cinchable neck for extra-cold afternoons, and a jumbo cargo pocket on the left side, perfect for carrying around dog leashes, bags of coffee, and whatever else I find myself toting around on a daily basis.
Certainly not the least-expensive thing on this list, but for something I wear five days a week or more, a price I’m more than happy to pay.
The $80 Suit — $80 (plus tailoring)
Exactly what it sounds like.
Written about here in great detail. I’ve since worn it on several other occasions, and I had a great time each time.
Vintage Armani Ties — $12/each
The perfect accoutrements for an $80 suit.
I bought a lot of four vintage Armani ties on eBay for about $40, plus one more (pictured on the left in the above image) for $15, so together they shook out to about $12 a pop. Made in Italy, 100% silk, in a variety of loud designs straight out of 1991. Kitsch-ish, but not kitschy. What else do you need?
I’d love to invest in a few Drake’s ties at some point, but until I’m wearing one day-in day-out, I’ll stick with vintage.
Henry’s Swoop Jacket — $669
A deeply satisfying splurge.
Every Henry’s piece is handmade in Toronto by owner Keith Henry. A few times a year, he drops a fresh batch of pants and jackets that sells out instantly. Given the limitations of his one-man operation, prices are necessarily high. But you get what you pay for. Everything Henry makes is simple, well-proportioned, and extremely well made. There’s an honesty to his approach. Making quality clothes takes time and money, a fact often obscured by international supply chains, questionable labor practices, and the noxious incentives of the fast fashion industry. This is the price you pay for ethical consumption.
The Swoop Jacket is Henry’s signature style. This particular specimen is cut from a heavyweight cotton moleskine in a pleasant shade of olive green. So far, it seems to go with just about anything: wool trousers, double-knees, and everything in between.
Simple, flexible, and utterly striking. I can’t wait to put some miles on this thing.