Certain elements of menswear remain firmly anchored in tradition. These timeless details, many dating back to the 19th century, continue to define style today. Michael Andrews recently shared his expertise in an article for Esquire, offering insight into three classic menswear features that have withstood the test of time: the button-down collar, cuffed trousers, and the “three-roll-two” jacket.
One of the most iconic shirt collars in menswear, the button-down collar has a rich history that dates back to the polo fields of 19th-century England. As Michael Andrews explains, the button-down collar was originally designed for polo players who needed a practical solution to prevent their collars from flapping up during matches. “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,” says Andrews.
While the button-down collar is often considered more casual compared to its stiff counterparts, it’s the perfect choice for those looking to skip the tie without sacrificing sophistication. The small buttons near the collar’s top edge provide stability, keeping the collar neatly in place and helping to frame the wearer’s face. According to Andrews, “The buttons lend stability to the collar, helping it to stand up and frame the wearer’s face.” This subtle but effective design feature adds an element of structure to a relaxed look, making it a go-to for modern-day gents who want to maintain style while feeling comfortable.
Another enduring menswear detail is the cuffed trouser, which continues to be a hallmark of tailored trousers. While some might see cuffs as an antiquated feature, Andrews explains their importance both in terms of style and function. “Cuffs add visual weight and balance to tailored trousers, enhancing the overall drape,” Andrews notes. This added weight helps the trousers fall more gracefully, making them appear more polished and well-tailored.
While cuffs don’t dramatically impact the durability of trousers, they do contribute to the garment’s longevity. The reinforced edge of a cuffed trouser can help extend the life of the fabric, making them a practical addition to any wardrobe. Andrews’ observations highlight how a small detail, like the cuff, can elevate the entire silhouette and provide a subtle nod to classic tailoring.
One of the most interesting details Michael Andrews discusses is the “three-roll-two” jacket, a silhouette that originated from practical adjustments to older three-button suits. Andrews explains that while some sport coats feature three buttons, the top button is rarely used. Instead, the lapel rolls over the top button, creating a distinctive look that appears as if the jacket only has two buttons.
“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,” says Andrews. What began as a practical solution for a style shift has since become a signature element of traditional American menswear. This subtle design detail reflects the dynamic nature of style—what starts as a practical solution can evolve into a fashion statement that endures through generations.
Photographs courtesy of Esquire
These classic menswear features, though centuries old, remain as relevant today as they were when they first emerged. Michael Andrews’ insights into the button-down collar, cuffed trousers, and the three-roll-two jacket highlight the lasting importance of thoughtful design and how small details can make a big impact on style. As Andrews notes, knowing how and when to deploy these elements is a critical part of dressing well, and they serve as timeless reminders of the craftsmanship that defines high-quality menswear.
