On the Enduring Bland Appeal of Brooks Brothers—and the Freaks Who Love It

The titular man from Mary McCarthy’s 1941 story “The Man in the Brooks Brothers Shirt” buys said shirts “a dozen at a time.” He doesn’t relay to the narrator that there’s any special appeal regarding their fabrics, or their construction—just that they’re readily available in bulk. He buys everything at Brooks, a habit his wife finds “stodgy”; the only distinctive feature about shirts is the monogram on the wrist, which he only has because monograms are gratis when the shirts are custom-made. The shirts, it appears, just happen to him.

Tom Yarbrough is a white Nashville businessman with a salt-and-pepper beard and the disposition of someone who would, similarly, happen into a lot of Brooks Brothers. And he does. He has more than 100 Brooks Brothers shirts, in fact, in every color and stripe and plaid imaginable, though he often defaults to blue. They hang and lay around his home, “stacks of ’em,” he says, proudly displayed on the Instagram he dedicates to them, @glengarrysportingclub. And he bought all those shirts on purpose.

Brooks Brothers shirts are not particularly collectible. For the most part, the company’s wares are decidedly nondescript and mass-produced. Further, there isn’t a huge difference between the preppy shirts that Brooks makes and the ones produced by its numerous competitors: oxford cloth, button-down collars (O-C, B-D), business-casual vibes. But in that mundanity, Yarbrough found something compelling enough to keep him coming back, over and over and over. ”There’s a power that maybe an article of clothing shouldn’t have,” he told me.

The company is just coming off its 200th anniversary. Skipping over the company’s brisk antebellum trade in outfitting human chattel, well-tread lore has it that a grandson of the founder went to an English polo match in 1896, noticed that players kept their collar points from flapping in the wind with buttons, and here we are. Who knows how many of them are floating around now. As soldiers took advantage of the GI bill during the 1950s, the Ivy League look proliferated.. Brooks originals like button-downs and soft-shouldered sack suits went mainstream, popping up campus shops, even in locales that didn’t have the prestige and tradition of the Ivies. When Ralph Lauren moved on from selling Brooks ties to found Polo, the Ivy look was the one he emulated—when Lauren wanted to call his tennis shirts “Polo” shirts, a name Brooks was already using the name for its button-downs. But Lauren was playful with the styles, nipping waists and slimming proportions. The spirit that undertook those tweaks was a sturdy-enough foundation for wide swaths of people to take things further. Carlton Banks leaned hard into assimilation in his Polo. The Lo Lifes leaned hard into bottom-up appropriation with theirs.

Yarbrough grew up in Oklahoma, near Tulsa, in the 1980s. The preppy look was ascendant, he remembers, and all of his friends were wearing it, Polo-down. But he didn’t get into Brooks specifically until after college, in the mid-2000s, when he was building his workaday uniform. He went into a Brooks store, didn’t like what he saw—British retailer Marks & Spencers’ purchase of Brooks in 1988 marked its transformation for many purists into a “mall brand”—and ended up finding something more to his liking when he visited a thrift store instead. He encountered the company’s older styles there and, spurred on by mid-2000s #menswear blogs, kept buying them up. ”A lot of us obsess not just over the company history, but also the details,” he told me. He parses the ubiquitous for anything that might make a given shirt more desirable. “I count buttons,” he said. “If you count seven buttons, it’s automatically inferior to a six-button.”

He’s looking for a canon, a rightness. “It looks right, it looks like a man’s shirt,” Yarbrough said. Perhaps there is no paragon of virtue, no collar more closely watched than the one perpetually framing Robert Mueller’s face from within a nondescript blue suit as he investigates President Donald Trump. Troy Patterson called his costume “the mark of an unreconstructed preppy.” Only Bobby Three Sticks, so staid, could pull off the high-wire act necessary to balance the excising of corruption from the highest levels of government with the reassurance that he’d preserve of the norms and institutions that failed to check that corruption in the first place.

Richard Carroll, an Armoury salesman and illustrator from Australia, warmed to the brand from afar, also through Ralph Lauren, and now he has fifty Brooks shirts. The Aussie version of the prep look, he told me, is a bit less formal from its American counterpart, tie-optional with RM Williams boots subbed in for Alden loafers. His love for Brooks, then, took on a cheeky affect. “There’s an ironic correctness to it that loses its connotations outside of Australia,” he said. About a week after he got his green card and arrived in America in 2015, he snagged his favorite shirt, a six-button yellow button-down. The unlined collar is worn through, the left shoulder once had to be sewn back on. But it’s harder in the US to separate people who like Brooks for fun from the people who wear it out of a sense of class duty. It’s difficult to imagine Brooks leaning into menswear’s preppy moment, which requires a level of irony that might alienate its core constituency. “If you see another guy,” Caroll told me, “and you can tell it’s a six-button…you just hope he’s not a raging Republican.”

The number of front-placket buttons or the presence of a collar lining (God forbid) are all determinants of whether a particular shirt hails from Brooks’s 1960s “golden age,” pre-M&S, when the company enjoyed a tonier reputation than the fusty one it has now. “For the first time in her life, she truly hated luxury, hated Brooks Brothers and Bergdorf Goodman and Chanel and furs and good food,” thought McCarthy’s narrator after a dour romp with Brooks Brothers Shirt Man. And she doesn’t just regret the romp because he’s a sad-sack traveling salesman from Cleveland, but because his politics grate her radical sympathies. “You people are crazy,” he tells her, “You’re never going to get anywhere with this proletariat stuff.”

The one genre of Brooks shirt that does lend itself to collectibility is the so-called “fun” shirt, patchwork numbers with mismatching panels of stripes or plaids or even solid-color pastels. They stand out not just for their garish hues, but because the clash so violently with the Brooks ethos. Legend has it that, in the 1970s, a Brooks executive saw a bunch of leftover fabric scraps from regular shirts being put together as practice for the shirtmakers. He made the franken-shirts available for the public, and they’ve been a mainstay ever since: Brooks recently created an online tool to customize them, a sort of Nike ID for oxford cloth. They’re fun because they’re a Brooks item that breaks character. They tell onlookers to “Go to Hell.” They’re incorrect.