The consumerist path of least resistance in America takes you to Amazon for books, Uber for transportation, Starbucks for coffee, and Pandora for songs. Facebook’s “Trending” list shows you the news, while Yelp ratings lead you to a nearby burger. The illusion of choice amid such plenty is easy to sustain, but it’s largely false; you’re being herded by algorithms from purchase to purchase. Here are the places you can spend money, the things you can wear: the shops contain certain things that change according to a set schedule. Your purchase goes in a bag with a logo printed on it. The logo says something about what’s in the bag, and something about where you shop—maybe even something about who you are.

James Jebbia founded Supreme, a cult clothing retailer, in New York, in 1994. He is a former associate of the streetwear pioneer Shawn Stussy, whose work from the eighties onward embodied a Zeitgeist originating in the surf culture of Southern California. You could describe it as unfussy but mindful of beauty and quality; athletic without being jockish; fun-loving, cheeky, male-focussed. Through its connection to Hawaii, California skate/surf culture has long-standing ties to Japan, and it also has strong bonds with punk and Oi! culture, with street art and tagging, and with weed culture. Stussy’s genius was in synthesizing these elements into a fashion identity and brand that found admirers far from Malibu and San Onofre.

Supreme, the most prominent of Stussy’s heirs, added a New York veneer of heightened exclusivity and sophistication to that legacy; it’s equal parts retail, art project, and hangout. The company announced its multifarious intentions right up front, with a red-and-white logo directly referring to the textual art of Barbara Kruger—an association the artist found reason to scorn, in 2013, when the logo was the occasion of a trademark dispute between Supreme and a rival clothing brand. But even that disconnect, in a way, somewhat embodied the sense of impudence that keeps kids lining up to buy the brand.

Supreme’s stuff is just a little expensive for what it is; T-shirts are priced at around thirty dollars, for example. But the goods are well made and the prices essentially fair, with clever designs expressing the brand’s signature breezy male athleticism, semi-rebellious attitude, and sense of fun. Kate Moss, Joe Louis, Black Sabbath, Charles Bronson, and Betty Boop have all made an appearance on Supreme merchandise. There are hoodies, sneakers, and off-the-wall branded goods, from pocketknives to fire extinguishers. Many of the designs are produced in partnership with a wide range of well-known artists, from H. R. Giger to Rammellzee to John Baldessari to Comme des Garçons. Each product is offered in a very limited run, creating a lively and lucrative secondary market, as David Shapiro reported for The New Yorker, in 2013. Twenty-odd years in, the brand is still expanding, with its tenth shop, in Paris, having opened a few weeks ago.

Into this context comes “Supremacist,” a new novel by Shapiro, who is now working as a corporate lawyer specializing in private-equity transactions; he spoke to me by phone on a Sunday afternoon, when I found him lawyerishly playing mini-golf “with a little putting green that I keep in my office.” (Shapiro is also the author of the popular, now-defunct Pitchfork Reviews Reviews blog and the novel “You’re Not Much Use to Anyone.”) The plot of “Supremacist,” such as it is, tells of a mildly unhinged New Yorker named David who is obsessed with the Supreme brand, and who persuades his rich, footloose friend Camilla to join him on a horrifically intoxicated pilgrimage to every Supreme shop in the world: in Los Angeles; London; Japan, where they make four stops; and back home in New York.

David is a social train wreck, getting drunk, taking too many drugs, falling asleep in the street, making blunderingly sexist comments, and swiping the snack of the passenger napping beside him on an airplane. In this way, David the narrator, who is at some uncertain remove from David the author, is a familiar American male character whose candor renders him appealing despite his unpleasantness, as we find in Bukowski, Miller, Mailer, Updike, Wallace, Heller, Franzen, and so on. The author (whose real surname is not Shapiro) really went on the trip described in the book, and really is a diehard Supreme fan. When I asked him what he had hoped to achieve with “Supremacist,” he replied that the trip had itself been the goal. “I paid my way by writing this book, and that’s what I wanted to do.”

The story amounts to a weirdly affecting critique of consumerism, half homage to Supreme and half culture-jamming. “Frankly, I find the brand to be like a brilliant art project, and also I find, obviously, some self-loathing in loving it so much,” Shapiro said. “I don’t know. There is some dissonance, obviously.” His feelings about the novel are similarly complicated: “I want to divorce myself from it because it’s so ugly, and depressing, but at the same time realizing that almost everything I say is exactly what would be expected for the narrator to say. I mean, I made this thing, and it’s so ugly, and I don’t want it to be anything like me, but it is who I am, to a great extent.”

Why would you feel that your book is ugly, when you’re so patently disgusted with the narrator’s materialist obsessions? I asked. The criticism presumably comes from somewhere else entirely, from a better place; you’re saying that this is gross, it shouldn’t be like this, it should be different—we don’t like being enslaved to things we can buy. “Yeah yeah, the character in the book is like, it is absurd to think that you could buy something and wear it, and it be a declaration of something intrinsic to you. It’s absurd!” Shapiro said. But later he described to me the dual nature of this character’s longing for an unattainable coolness, finding that ridiculous, impossible, but still hoping it’s not. “Supreme is the coolest thing, in a way, to the narrator—you know, and to me—and he goes on the trip in the hopes of absorbing it, through, like, osmosis,” he said. “Like sitting there long enough and just popping out, one day, a cool guy. Not only a cool guy, but like . . . well adjusted, and, you know? All the things that the brand promises.”

Surely all clothing is aspirational to some extent. What you wear, how you speak, how you cut your hair, how you educate yourself all create a personality, a way of being in the world that you yourself can stand. All this is silly and artificial, but also not—it’s also serious, and has a meaning. There’s who you are, and how you express your life, just by living, and then there’s the manufactured sort of carapace that you’re making deliberately, to show to other people, to signal to them various things.

I tell Shapiro about the arguments I’ve had with my elderly mom on this score, like when she expresses disapproval of a waitress’s tattoos, and I tell her, Look, this is not for you; just like when you used to complain about whatever glam-rock garbagio I was sporting in the seventies (and yes, that is how long we have been arguing). Not for you! You are not the audience for these tattoos, for those long-ago-torn fishnets. Why do you think this lady would be trying to wear something that you would like? You have nothing to offer this person. You don’t have anything she wants! She is communicating to someone else. So part of it’s real, then; when some teen-ager buys the Supreme skateboard deck, or the shirt, what’s really going on is that he’s showing all his friends, I’m this kind of person.