Not to sound like a group of black-light-poster-and-bong enthusiasts, but have we ever really thought about the buttons on a button-down collar? Like, really thought about them? What about the top button on a sport coat that doesn’t seem like it’s meant to be buttoned? And not to blow our minds or anything, but why do we cuff trousers, anyway?

Okay, fine. Dorm-room stoner vibes might not be the first thing we associate with a trio of hallmarks of classic Ivy style. But the questions are valid. How did these details come to be in the first place? Why did they become preppy stalwarts? And whether we vibe with Ivy style or not, how should we be considering them when it comes to our own look?

That’s what we set out to explore after realizing, upon looking at a photo of a very stylish guy in a three-roll-two jacket, that we had no firm understanding of how this sartorial quirk—in which the top button of a three-button jacket “rolls” under the lapel so it buttons like a two-button jacket—came to be.

When it comes to men’s style, details matter. With the notable exception of avant-garde fashion, most of the clothes we wear are rooted in history and shaped by long-standing cultural codes. It’s fine—even encouraged—to subvert those codes. But to do it right, we have to understand where things came from. Plus, let’s be honest, it makes for great cocktail-party banter (if the cocktail party is full of fellow menswear enthusiasts).

Of course, when exploring the origins of clothing, lore and legend abound. Sometimes a story is so good that it becomes part of the very (ahem) fabric of menswear mythology, even when it’s not entirely true. That said, the explanations we found are the most plausible, cosigned by experts in the field. So, let’s break it down—where these details came from and how we should wear them now.

Button-Down Collar

Just so we’re clear: A button-down collar refers to a collar that stays in place thanks to two small buttons near the top of the shirt. The style originated in the late 19th century, according to Michael Andrews, founder of Michael Andrews Bespoke. “Famously, it’s credited to polo players in England who sought a practical way to keep their collars from flapping up in their faces during matches,” he explains. “It was later popularized in the United States by Brooks Brothers when they introduced their version in 1896. Ironically, that was the ‘original polo shirt,’ not the piqué mesh shirts most people think of today.”

Nowadays, it’s more closely associated with traditional American style than with the British fields where it originated. “For a lot of guys, it’s coming back to the idea—even if we have British clients—of American, trad style,” says Jake Mueser, founder of the New York–based tailoring brand J.Mueser. “We also get a lot of British guys and a lot of California clients who enjoy the stark contrast of going for this Northeast, Ivy style while being in the tech world in San Francisco.”

As for how to wear it? Well, the first thing to remember is that the button-down collar is considered more casual in many parts of the world, especially in England and Europe. In the U.S., thanks to its history, we can dress it up or down. Andrews calls it “the Swiss Army knife of shirts” because of its versatility.

Can we throw it on with a suit and tie? Absolutely. But let’s make sure it’s not a genuinely formal affair. If we’d like to skip the tie, it’s a great option; as Andrews notes, “the buttons lend stability to the collar, helping it stand up and frame the wearer’s face.” And while Mueser doesn’t advocate for breaking from convention too often, he does approve of leaving the collar points unbuttoned from time to time—a move beloved by Italians since the middle of the 20th century, according to Esquire’s own creative director, Nick Sullivan.

“I think it’s cool,” Mueser says. “But there has to be a certain kind of ease in how we do those things. It’s not like, ‘Oh, I’m going to go get a button-down collar and wear it unbuttoned.’ Sometimes we wear it buttoned, sometimes we don’t. It has to look a certain degree of unintentional.”

Three-Roll-Two Jacket

Here’s what we mean when we say “three-roll-two jacket”: Some sport coats have three buttons, but the top button, though functional, is rarely if ever used. Instead, it rolls gently to create an appearance that the jacket has only two buttons instead of three.

The origin of the three-roll-two jacket depends on whom we ask. It may have gained popularity over the first half of the 20th century or been established more specifically at the turn of the century thanks to a group of style-minded college guys without a whole lot of money to buy new clothes.

“While its precise origins are debated, it’s closely associated with Ivy League style and Brooks Brothers,” says Andrews. “Legend has it that as the two-button jacket gained favor, many men with older three-button suits naturally allowed the lapel to ‘roll’ over the top button, creating the distinctive three-roll-two silhouette. And what started as a practical adjustment became a hallmark of traditional American menswear.”

Thanks to the American–Italian cultural crosscurrents that led to the unbuttoned collar points, it’s also become a staple of Italian tailoring. “The core of our line is three-roll-two,” explains Mueser. “I think it’s a nice confluence between this classic, American, Brooks Brothers feel but also something that’s been adopted by the Italians. I also find it practical. Ninety-five percent of the time we wear it with just the middle button, but in the shoulder seasons, we find ourselves—especially with tweeds and cashmeres—popping the collar up, rolling the button over, and making it warmer that way.”

As for when to pull that move? “Just remember, this is one menswear rule we should still follow: Sometimes, Always, Never,” says Andrews. “Sometimes we do up the first button, like in cold weather or strong wind; always button the second, although we won’t hold each other to it; and never button the third.”

Trouser Cuffs

Trouser cuffs, of course, are the inch and a half or so of fabric at the bottom of our pants that’s folded up and stitched. What’s the origin story of this style move? “There’s so much conjecture,” Mueser says. “Maybe someone rolled their pants up. And then someone else was like, ‘Oh, I’m going to roll my pants up.’ And then everybody started rolling their pants up.” Turns out, he’s kind of right.

“Trouser cuffs or ‘turn-ups,’ as the English like to say, date back to the late 19th century and are often attributed to King Edward VII, who allegedly turned up his trousers to avoid getting them muddy,” says Andrews. “The practice gained traction and became a sartorial statement rather than just a practical solution.

“Cuffs add visual weight and balance to tailored trousers, enhancing the overall drape,” he continues. “They also provide practical benefits, with the extra fabric adding weight to improve how the trousers fall. While they don’t significantly impact durability, the reinforced edge can extend the life of the trousers.”

Though the standard is usually one and a half to one and three quarters inches, the size of the cuff—something that a true “menswear person” is more likely to opt for than someone just looking for a basic suit—is very much dependent on build and preference.

“If we’re six-two, six-three, a two-inch cuff might work,” says Mueser. “But if we’re five-seven, five-nine? A two-inch cuff is a lot of real estate on the leg. We generally opt for one and three quarters. It’s amazing what a fraction of an inch can do to proportions.”

At the end of the day, knowing the history of these details helps us make smarter style choices. Whether we embrace them, tweak them, or ignore them altogether, at least we know what we’re working with.