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“What is that, 16 pairs of cycling bibs?” This is the question Mac Bishop asks as we survey the morass of spandex spread across my bed. “Something like that,” I say sheepishly. “And I think there are a few pairs in the laundry.”

It’s a weirdly humbling experience to have another man, a Birkenstock-clad, practicing minimalist from Portland, Oregon—one you have just met (and who, at 29, is some twenty years younger)—sift through your clothes. It’s like sitting naked with a stranger in a metaphysical Turkish bath of the soul. I suddenly find myself explaining, too vehemently, why my closet is the way it is. That blue shirt from Uniqlo? I liked it so much I bought five. That Breton-striped pullover with the weird sleeves? I thought, you know, if I’m ever in in summer, I will so totally fit in. That pair of pants, purchased on sale, with the strange stitching I thought no one would notice? I notice every time, so I never wear them.

There could be a whole psychology textbook written about the closet. In its confines we find the warm glow of nostalgia (that ragged half-marathon finisher T-shirt) and the optimistic projections of our future selves (the skinny jeans that don’t quite fit); we grapple with the terrors of decision regret and loss aversion (it feels worse to lose something, in the moment at least, than it feels good to gain something). We are “strangers to ourselves,” says psychologist Timothy Wilson, explaining the psychic murk under-lying much of our behavior—exactly how I feel when Bishop asks when I last wore a certain item he’s holding and I can’t fathom the answer. One expert from California Closets recently told that people regularly wear, on average, about one-fifth of the clothing they own.

Up until the cycling bibs, my closet audit was going reasonably well. “This is looking fairly minimal already,” Bishop had said at the outset. For that I largely have the constraints of my Brooklyn apartment to thank—no garage or walk-in closets here. (In a version of Parkinson’s Law, stuff seems to magically expand to fill the space dedicated to it.) But then we opened the drawer into which a couple dozen cycling kits had been crammed, springing forth like novelty snakes from a peanut can. “It’s easy to collect and not throw away soft goods. They seemingly don’t take up too much space,” Bishop says. “With hard goods, it’s not like you have two coffee makers in your kitchen.”

I ride bikes a lot, and I sometimes write about riding bikes, so it was easy to justify the nonstop acquisition of cycling stuff—as the joke goes, the ideal number of bikes is n plus one. But had I crossed some threshold? Like most of the world, I knew that Marie Kondo’s book had inspired any number of readers to “KonMari” their closets and then share their experience. But the accounts I’d seen didn’t seem relevant to my situation: in my mind’s eye, these were primarily women dispensing with once fashionable shoes and tops that had lost their ability to “spark joy.”

No, my cycling stuff wasn’t mere clothing. This was gear. I needed it to do things. That justification tidily skirted the question of exactly how many cycling outfits I needed. If I could make do with just one while traveling (pro tip: take a shower, and drink a beer, in your kit), did it not seem odd to have several dozen at home? Were they enhancing my life or making it more difficult, expanding my array of choices and thereby increasing the amount of time necessary just to find what I’d chosen?

Mac Bishop is no professional organizer. Cleaning out closets isn’t even his side hustle. But I’d invited him into my home after reading about his provocative “wardrobe experiments,” which raised interesting questions about how much stuff we really need to get by. In this he is hardly unique: the internet, in heady corners like Reddit’s Minimalism forum, brims with exploded-view images of “capsule” wardrobes, of the carefully curated gear bags of digital nomads, of decision-fatigued Silicon Valley types who’ve pared their daily wear down to a single uniform—sartorial Soylent. What makes Bishop’s less-is-more ethos unusual is that he spends most of his time trying to sell clothes.

In 2011, after graduating with a business degree from Cornell University, Bishop found himself employed by , the consumer-product giant, in New York City. Like many young office workers, he grappled with the tyranny of professional attire—-acquiring a sufficient variety of costly button-down shirts, paying the steep dry-cleaning bills, buying more shirts to wear while the others were at the cleaners.

On a whim, he began wearing a brown-wool houndstooth Sir Pendleton button-down, a dressier version of the ruggedly iconic shirts made by Pendleton Woolen Mills. (The Beach Boys initially called themselves the Pendletones, by way of homage.) Bishop’s family owns Pendleton, which was formally established in 1863 by his great-great-great-grandfather. “It changed the way I dressed,” he says of the shirt. “I didn’t have to go to the dry cleaner every day. I didn’t even have to hang it up. That thing was a beast.” While it was hardly traditional wear at Unilever, Bishop says that the shirt—which he tailored for a slimmer fit—drew compliments, in particular for its just-pressed appearance, which belied the fact that it had never seen an iron.

Inspiration took root. “It got me thinking,” says Bishop, “that wool could have an impact in the business-casual market and just make guys’ lives easier.” He was, of course, no stranger to the material. And wool had come a long way since the days of the heavy, scratchy Pendleton shirts hanging in vintage stores. Merino wool, after centuries of selective breeding, was as soft as cotton, with a greater capacity to manage moisture and odor. Bishop watched as brands like Ibex and Icebreaker brought merino to the outdoor market, doing a lot of the heavy lifting to educate consumers.

The idea persisted even after Bishop left Unilever and was dabbling in an online art startup. As proof-of-concept, he launched what he dubbed the 100-day challenge. Over a span of three months, he would outfit his upper half in nothing but the Sir Pendleton, neither washing nor ironing it. When it was over, Bishop—tall, affable, and boyish looking—took to the streets to solicit feedback (tactile, olfactory, and otherwise) on the shirt. The resulting video became the centerpiece of a 2013 Kickstarter campaign for his new brand, , which promised a better button-down, one that was “naturally anti-wrinkle and odor-fighting.”

A blue oxford hardly seems revolutionary, and indeed, the Kickstarter goal was modest: $30,000. (Bishop says he was hoping for $75,000.) But the campaign caught fire. Soon there were Japanese TV reporters holding their noses to Bishop’s armpits, while Letterman and Leno riffed on the shirts, the latter cracking jokes about underwear and New York City cabbies. Bishop found himself having to do reverse press—tamping down the assertions made by some media outlets that he had invented a new wonder material. After a little more than a week, as the campaign approached $300,000 in pledges, Bishop, fearing he might exceed his capacity to deliver, shut it down.

On the face of it, the appeal was simple. As Bishop notes, the men he spoke to wanted their shirts to be like jeans—easy to care for, flexible. But there was also something more subversive going on. We have become inured to the idea that clothes need to be kept at near Febreze levels of freshness, that to wear the same thing two days in a row is a sign of irredeemable slovenliness, that to arrive at work slightly damp from a bike ride requires instant decontamination. We Yankees, famously, seem to suffer from a particular obsession with cleanliness (devastatingly captured by novelist Graham Greene in , as his cynical British-journalist narrator eyes two American women, wondering, “Did they take deodorants to bed with them?”).

But cycles of washing and drying are notoriously hard on clothing. And what precisely are we vanquishing? A Canadian professor of textile science, testing a pair of jeans that a student had worn for more than a year without washing, . In an Australian study that asked subjects not to launder their jeans, the researcher concluded that “the expectation of not washing was more repulsive than the actuality.” In other words, people were washing their clothing—and hastening its obsolescence—more out of habit than necessity.

A change of habit is often enabled by a change of context. Two years after launching Wool and Prince, Bishop relocated to Portland for personal and business reasons. He was in the process of moving between houses in the city one day when he decided to pack his most crucial wardrobe items into a single box. An idea began to form. Could he get by for a year with just this box? His 100-day challenge had opened the door to a deeper question: If he could wear the same shirt for that long, how much clothing did he really need?

Bishop pared his wardrobe to 26 core items (excluding some athletic apparel and a suit he wore to a wedding) and stuck to it for the next 365 days. It helped that he was working mostly out of his home and living in a temperate climate. Still, three pairs of underwear for an entire year? “Air ’em out,” he says, “and sleep naked.” He adds: “I wouldn’t wear them multiple days in a row.” Still, he says, “I was doing more laundry than I would’ve liked.”

To document his process and to further explore what he was experiencing, he set up , an online community for aspiring minimalists. It’s mostly made up of Wool and Prince customers, many of whom had, in the wake of Bishop’s video, taken up the challenge of wearing Wool and Prince shirts for extended periods. (One company field tester, Jens Rasmussen, reported wearing his gray work shirt for 33 consecutive days of hard bush living while filming a National Geographic show in the Serengeti, even earning a reputation, as he wrote in a post, as “the best-dressed guy on our expedition.”)

The site reads like a mashup of efficiency guru Tim Ferriss and thrift maven Mr. Money Mustache, with posts on everything from Swedish death cleaning (don’t leave all that junk for your heirs to sort through) to declaring sock bankruptcy (tossing your mismatched collection and bulk-buying a new supply). It taps into some of the currents of minimalism already flourishing on the internet. There are scores of wardrobe pursuits—the ritualistic world of “one bag” travel (i.e., don’t pack more than one bag), the almost Platonic search for the perfect item of clothing, obviating the need for all others and resisting the tides of fashion and the scourge of time. For instance, a massively popular five years back was soon followed by a . (One maker even advertised a 100-year hoodie for would-be centurions.)

Like the tiny-house movement, minimalism can be one of those things that people are far more apt to talk about doing than actually do. But it isn’t hard to understand the impulse. According to Forbes, the average number of outfits in an American woman’s wardrobe has increased more than threefold since the 1930s. This is a result of ever cheaper clothing (even as our wardrobes have grown, the share of household budget we spend on clothing has plummeted) and increasing home (and thus closet) size. Findings from behavioral psychology, meanwhile, show that however good it feels to acquire all that stuff, the hedonic payoff is mostly short-lived. The closet becomes a reproach, and we sift through increasing numbers of things we no longer want.

Bishop is cognizant of the various contradictions of minimalism: that its conscious adoption often reflects privilege (Thoreau had his family pencil-making business behind him); that it can perversely lead to status-seeking one-upmanship; that it’s frequently marketed as just one more purchase away (one minimal-living author has five minimal-living books listed on Amazon). Patagonia’s famous Don’t Buy This Jacket campaign in 2011, however well-intentioned, coincided with the brand’s robust expansion. (“In short,” noted Businessweek, “the pitch helped crank out $158 million worth of new apparel.”) Bishop is even a little leery of the word minimalism itself, which, like sustainable, is in danger of being denuded. “There’s no sustainable clothing purchase,” he argues. And he is aware that his business, which has seen average annual growth of about 50 percent, is predicated on people adding stuff to their wardrobes. Many of the Only What Matters posts are, after all, written by people looking to buy things. “Start with what you currently have in your closet,” he counsels. “Don’t run out and buy all the minimalist clothing you can find.”

Before Bishop’s visit to my home, I had been doing my own little wardrobe experiment, wearing one of his company’s merino-wool polo shirts (instead of the nine others I had on deck) for most of a typically warm late-spring month in New York: on sultry subway platforms, on five-mile bike commutes, while playing soccer with my daughter in the park. Dawn to dusk, for weeks, no washing, no ironing. Does it smell? My wife, my most reliable witness, reports no. Has anyone noticed my monotonic wardrobe? We flatter ourselves. Via the psychological phenomenon dubbed the spotlight effect, we overestimate how much the world takes notice of us. (One of the original experiments looking at this featured, wonderfully, a subject wearing a Barry Manilow T-shirt.)

“Don’t pack your fears,” goes the slogan in the world of ultralight hiking. On the trail, the lower your base pack weight, the easier your life will be, the less energy you’ll expend, and the less you’ll think about what you’re carrying. I’ve been trying to conceive my closet as a backpack, my life as an expedition. To get my base life weight down, off to eBay went scores of cycling clothes (the pre-owned market is surprisingly robust) and a Burberry suit, bought on sale, that I thought I might want (that future self never arrived). What didn’t seem saleable went to that nearest and most effective redistribution channel: the sidewalk, where, in Brooklyn, things vanish faster than a New York minute.

I have taken to heart other suggestions from Bishop, like a one-in, one-out ethos and organizing things by genre. (Why was my ratty outdoor-work outfit kept with my normal clothes, thus adding to the visual and cognitive noise, rather than in my tool area?) So far, at least, my efforts at reducing my base life weight have been a success. My closet now looks less like the discount bin of a thrift store and more like the new-arrivals rack at a spare SoHo boutique. Ironically, even as I’ve lost things, I feel like I’ve gained a more appreciative form of materialism. For the first time in years, I possess a real sense of what I have.