Crackpots #10: A Few of My Favorite Things (Patreon)

Hello friends,

Yung Chomsky here. This month I'm going to be a bit less philosophical, a bit more grounded. I'm going to do a little show-and-tell: I'll show you some of my favorite pieces of clothing from my closet, and I'll tell you why they're special to me. This is not a holiday gift guide; you're not going to find any affiliate links or things of that nature here. But who knows, maybe this will inspire you to seek something out. Or maybe it will have the opposite effect — maybe you'll hate all of these things, and this will help you know what to avoid, which is also useful. Or maybe none of this will have any relation to the type of clothes you wear, or anything you care about; there might be something here for you all the same. My aim is not to tell you how to dress; I just think it's fascinating to know not only what other people like, but why they like it.

Now, I like clothes, but that wasn't always the case, as anyone who knew me in my teens or twenties would confirm. I wasn't brought up to know or care about this stuff, and I didn't have any role models for it. I used to wear what people gave me, and having to shop for my own clothes gave me serious anxiety. I won't bore you with a long narrative about my personal style journey; I will, however, begin by telling you a few reasons why fashion fascinates me in general.

First, there is the basic aesthetic beauty of patterns, textures, colors, silhouettes. I'm not equipped to give a very full explanation of this — I'm not sure if anyone is. I could talk about color theory or something like that, but as far as I'm concerned, some things are just pretty and I like looking at them. It's like faces; it's hard to explain why I enjoy looking at a beautiful one, but I know that I do. One thing that's worth mentioning here, though, is that I think a lot of this dimension can be flattened when looking at still images. A still image can give you a sense of what a garment looks like, but not really how it feels, how it moves. And it's just these hard-to-convey qualities that can be the entirety of the difference between a mediocre garment and a superlative one. Product photography can be deceptive in either direction, which is why I think it's always better to shop in person. I've seen and touched plenty of high-priced pieces of clothing that didn't impress me, but I've seen equally as many expensive items where the online store listing left me cold, but the appeal instantly clicked when I handled them in person.

Beyond that, there's the (for lack of a better term) sociohistorical aspect of fashion. Any given garment carries with it a rich lineage: a time, place, and context in which it was developed, and the way it evolved over time. We often recognize these associations even if we wouldn't know how to describe them, and never learned them explicitly; they're absorbed via cultural osmosis. These connotations create expectations in a viewer, and where there is an expectation, there is an opportunity (in this case for both the designer and the wearer) to deliver either satisfaction or surprise. In a very similar way, anyone who was raised on western, tonal music has ingrained in their auditory processing apparatus certain ideas about melody, chord progression, rhythm, and so on. We hear a particular series of chords as implying a certain resolution. The composer can deliver on that resolution or they could subvert the expectation. This is, I think, a big part of why the restrictions built into a system of expression can enhance rather than dampen that system's ability to continually product interesting and novel output. In other words, in order to be a boundary-pusher, you need boundaries.

I could go on all day in this vein, but let's leave it there for now and get to some pictures.

Donegal Tweed Overcoat

  This is a Balmacaan — a loose-fitting overcoat with raglan sleeves. This one is made in a brown herringbone Donegal tweed. Capital-D Donegal is a place in Ireland where this kind of fabric has been produced for a long time, but small-d donegal has come to refer to the nature of the fabric: It has a base color with small specks of yarn of other colors mixed in. This coat lacks those characteristic flecks of color, but I still enjoy the way the irregularities in the tweed tell a subtly different story from up close than from a distance. It was made by Magee, an Irish maker. I don't know what year it's from, but they still sell what appears to be the same coat. The new one seems to be $700, which I think is very reasonable for a coat like this; I would tend to expect a new coat like this to be at least $1,200. There's a little "life hack" for you here: It turns out that making clothes is a very different undertaking from selling clothes. Thus the maker and the seller are often entirely different companies, although it's not always a totally clean separation, as the people doing the selling might be the ones coming up with the design. Sometimes the designer is making some tweaks to the maker's standard pattern, resulting in something slightly unique to them. Other times, the designer is just putting their logo on the standard garment that the maker produces. The upshot is that sometimes you can buy something directly from a manufacturer's janky website with ugly photography, or from a designer's slick web site which has great imagery and slick branding, and the former will be significantly cheaper. This coat looks like an example of that phenomenon. For another: This fair isle vest is made by Jamieson's, who will sell it to you for about $160; or you could buy it from Drake's for $425.

Anyway, back to my overcoat. I bought it in 2020, soon after I first moved to New York. I didn't need a real winter coat when I lived in San Francisco. It's lined and quilted. Its collar is substantial enough to stand up, which both looks dramatic and protects your neck against the wind. And, perhaps most importantly, it's full and it's long, which is to say it reaches below my knees. Without going on too much of a recent-fashion-history tangent: around the turn of the 21st century, several prominent designers started producing tailored clothing with a slim or “shrunken” silhouette. This eventually filtered into the mainstream and became the dominant style. And so the median man’s coat produced in the past couple of decades is cut quite slim and short, even though a longer coat is better for warmth and a fuller coat can fit over layers, as an overcoat is meant to. I think this coat would probably be even cooler if it were another inch or two longer, but it’s still vastly better than so many modern versions that barely cover your ass.

I purchased this coat at Crowley Vintage, which is a highly curated vintage menswear shop in Brooklyn. I think I paid around $400 for it. That's certainly not a thrift-store price, but Crowley isn't a thrift store. I could write an entire essay on the economics of clothing — or someone else could, anyway. In fact, I think someone very famous once had a bunch to say about lengths of fabric and coats. But I'll leave that for another time. What I will say on the subject is that there's an aphorism about how when you're buying any product or service, you need to pick two out of these three: fast, cheap, and good.

I think this applies to clothing as much as anything else, with some specific gradations to consider. "Good" in this case can be thought of as encompassing both quality of the product, and quality of the production conditions. While a high price by no means guarantees good conditions, there is also a price floor beneath which good conditions are impossible. And I don't think anyone is making a coat of this quality today and selling it for $400 or less. As far as "fast" is concerned: the fastest route would be to buy something that's currently in production, either online or from a physical store. Less fast might mean buying something that isn't currently produced from a specialized shop, like Crowley Vintage. And even less fast than that might mean hunting around at thrift stores, estate sales, small online sellers, etc. The more patient you're willing to be, the better deal you're able to get. I enjoy the thrill of finding something great for a killer price, but I'm also willing to pay for someone else's time and effort at curation.

In any case, this overcoat has kept me warm for four NYC winters running, and I expect it to serve for many more to come.

Pendleton Bomber Jacket

 Pendleton is a venerable American company that still weaves woolen fabrics in the Pacific Northwest. From blankets to Beach Boys, you've probably seen Pendleton before, even if you don't recognize the name. I bought this one at the Alameda Point Antiques Faire in 2015, soon after I moved to San Francisco. I think I paid $100 for it. I had only somewhat recently begun to care more about the things I wore. One of the friends I was attending with spotted the jacket and told me it would look cool on me. I remember thinking, would it? Is this a cool jacket? I felt like I was really going out on a limb by buying it. I've sometimes come to regret purchasing things that gave me that feeling, but not this one. It's a perfect jacket for the Bay Area — not too heavy, but keeps you warm when you need it. It has a full fit without being too oversized, and the pattern is distinctive while still feeling classic. Strangers have often commented on this one when I've worn it. I also wore it on my very last day in San Francisco before I moved away, pictured here:

Polo Ralph Lauren 5-pocket Cords

 These pants were the result of one of those patient hunts. I got these on eBay last year for $60. I had been looking for the perfect pair of five-pocket corduroys — that is, corduroy pants that are cut like jeans, rather than dress trousers. There's a list of things I'm looking for with a pair of pants — I can't do a low rise or an overly tapered leg. And of course there are many types of cotton corduroy. The fabric will sometimes be referred to by the wale count, i.e. 8-wale or 10-wale. The wales are the ridges that give corduroy its distinctive design, and the wale count indicates their width by telling you how many fit in an inch.

These were made by Polo Ralph Lauren, one of Ralph Lauren's primary labels. I believe they were made in the 90s but I'm not certain. I'm a Ralph Lauren fan; I've collected a lot of pieces from them, and their influence is visible in the work of many other designers I'm fond of. That said, I'm not a Ralph historian, like some people who can give you a detailed breakdown of all of the sub-labels and eras which ones were the best and so forth, but I do have a general sense of those things. The important thing to understand is: If you go to eBay or etsy or wherever and just search "Polo Ralph Lauren corduroy pants," you'll find a lot of things which may look superficially the same but were made in different factories at different times and vary significantly in the details.

I had some intel from a friend that the made-in-Singapore cords would have the qualities I was looking for, so I kept scouring until I found these. They're soft and substantial and fit me just the way I like. Buying vintage online is inherently a gamble, but it's made slightly less so by paying close attention to measurements. Get a tailor's tape, measure something you have that fits you well, and compare to the listed measurements. Message the seller if they don't put them in the listing.

Now I should perhaps clarify that I don't exclusively wear vintage clothes; I'd guess that about half of my wardrobe was purchased new, with the other half being secondhand, if not vintage. But, I think for obvious reasons, it's easier to feel like a vintage item is special, which makes it easier to talk about.

There are many more pieces I could write about, but I think that's enough for this month. Perhaps this will be a continuing series; what do you think? Sound off in the comments etc. Until next time,

YC