One of my favorite shirt styles is the button-down collar shirt. This style is most closely associated with the Oxford cloth button-down, known as the OCBD among traditional menswear enthusiasts. Variations on this collar style abound. The collar points can be short or long, the collar roll subtle or pronounced.

The button-down style likely originated in the late 19th century on the polo field, where the collar buttons served to prevent players’ shirt collars from flapping up into their eyes. Today, button-down collar points are generally shorter and the dangers of one’s collar points flapping into one’s eyes virtually nonexistent. Yet the button-down collar continues to be popular. In this article, I’ll explain how to create the collar look that epitomized Ivy League style and, among purists, remains the standard.

Photos of ready-to-wear button-down shirts can help you decide what style collar roll you prefer. The roll…