The button-down shirt is one of the most important pieces in Ivy style. Simple, comfortable, and versatile—it’s the shirt that changed menswear. A small detail, two buttons on a collar, created a look that has lasted more than a century and continues to feel modern today.
From Polo Fields to Campus
The story began far from American colleges. In the late 19th century, British polo players had a problem. While galloping across the field, the long collars of their shirts flapped in the wind and became a distraction. The solution was simple: attach small buttons to hold them in place.
In 1896, John Brooks of Brooks Brothers noticed this detail during a trip to England. He brought the idea back to America and designed what became the first oxford cloth button-down shirt. Compared to the stiff, detachable collars most men wore at the time, this new shirt was soft, washable, and practical. It immediately felt different—less formal, more modern.
Casual but Smart
By the 1920s through the 1940s, Ivy League students discovered the shirt and made it their own. They paired button-down oxfords with navy blazers, grey flannel trousers, or khaki chinos. On their feet were penny loafers or brogues instead of shiny black dress shoes.
The effect was casual but smart. It wasn’t formal business wear, but it wasn’t sloppy either. It had ease, confidence, and a hint of sport. This balance became the foundation of Ivy style—a way of dressing that felt effortless yet respectable. On campuses from Yale to Princeton, the button-down shirt became almost a uniform.
Ivy Goes Mainstream
By the 1950s, Ivy style left elite campuses and spread across America. After World War II, more young people entered universities, and the button-down shirt became tied to a new, democratic way of life. It was no longer only for wealthy students—it became a part of everyday wardrobes across the country.
Jazz musicians also loved the shirt. Miles Davis and other players often wore Ivy staples like oxford shirts and narrow ties. In offices, men swapped their stiff collars for button-downs, enjoying the comfort without losing respectability. At night, the same shirt could work in a jazz club or a dinner date.
The Ivy wardrobe of the era—oxford button-down, knit vest, penny loafer, grey flannel suit—is still recognizable today. These items shaped how American men dressed for decades.
Across the Ocean
The style didn’t stay in the U.S. In the 1960s, Japan discovered Ivy through Teruyoshi Hayashida’s photo book Take Ivy. The images showed American students walking to class, reading on the lawn, or gathering at cafés—always in button-down shirts, chinos, and loafers. For Japanese youth, it was more than clothing; it was a window into a modern lifestyle.
At the same time in Britain, young people picked up Ivy elements too. For them, the button-down represented something fresh and international, different from their parents’ formality.
Rise, Fall, and Return
Ivy style reached its peak in the mid-1960s. Soon after, it began to fade as new countercultural looks took over. By the 1980s, Ivy had blended into what people called “preppy” fashion. Brands like Ralph Lauren revived the look but also tied it back to privilege and wealth.
Still, the button-down shirt never disappeared. Brooks Brothers, J. Press, and L.L. Bean kept producing it year after year. For many Americans, it became an unofficial uniform—just as natural as a pair of jeans.
Back Again
In the 2020s, Ivy style is back in the spotlight. People are searching for clothing that feels timeless, versatile, and rooted in history. The button-down shirt offers all of that. It works at the office, on the street, or in a café. It can be worn with a suit, with chinos, or even with jeans. Few garments have that kind of flexibility.
What makes it special is not just its look but its story. Born from a sports need, adopted by students, spread by musicians, reinterpreted globally—it has crossed cultures and generations without losing its identity.
A Small Detail, A Big Story
At first glance, two small buttons on a collar seem insignificant. Yet they carry over a century of style history. They link polo fields in England to Ivy League classrooms, American jazz clubs, Japanese sidewalks, and today’s global fashion.
That’s why the button-down shirt is more than just a shirt. It’s a piece of culture, a symbol of Ivy style, and proof that small details can change the way the world dresses.