Button-down dress shirts: history, style tips, and expert advice

Let’s talk dress shirts, fellas. More specifically, let’s talk about the button-down dress shirt. Before you ask, no, not all dress shirts are button-downs. Most guys, including me, had no idea that there was a difference between a button-down and a button-up.

When you say button-up, you are referring to any shirt that buttons up the front, a front closure that is present on dress shirts, sport shirts, and even cardigans (which are button-up sweaters). A button-down is any shirt that has a collar secured in place with buttons. So, all dress shirts are button-ups, but not all dress shirts are button-downs. Clear as mud? Ok, great.

Now, let’s talk about the lasting legacy of the button-down dress shirt, which celebrates 125 years being a staple in the man’s wardrobe. For that, we reached out to our friends over at Robert Talbott and Nick Picchione, Senior VP of Merch and Design, for help.

I believe the lasting legacy of the button-down shirt is largely due to its extreme versatility. It perfectly bridges the gap between dress and sport and is always appropriate for all but the most formal occasions. – Nick Picchione, Senior Vice President of Merchandising and Design for Robert Talbott

The lasting legacy

So much of our fashion nowadays derives from our love of military and sport. The trench coat from the trenches of WWII, the polo shirt from the tennis courts, and the button-down is no different.

Founder of Brooks Brothers, John Brooks, noticed polo players in the late 1800s sewing buttons onto their collars to keep them from flapping during their matches. He brought the style to America, and it took off, playing a vital part in the man’s wardrobe ever since.

“It looks good with or without a necktie, with or without a jacket, with the sleeves rolled up or down, tucked in or hanging loose. It always works. Fabric is part of the equation, especially in a classic Oxford cloth that really does get better with age,” Picchione says.

“It’s uniquely durable, but also distinctive,” he adds. “Classic details like a chest pocket for functionality, an applied front placket, and the rear box pleat are all details that helped build its iconic status. Its slightly utilitarian and non-fussy attitude makes it uniquely American in design and sensibility. It has both a modern and an old-world feel. Style icons from JFK to Andy Warhol to Fran Lebowitz helped cement the button-down as a wardrobe staple that continues to inspire. Everyone looks good in a classic white Oxford button-down shirt. Everyone.”

Rules for the tie

When I used to sell suits, many men (for some reason in the IT or engineering spaces) wanted their dress shirts to be button-down. They always said they wanted to make sure their collars stayed in place and didn’t “fly away.” I will be honest, it makes sense to me that polo players needed to keep them in place during matches, but I never understood the amount of wind and sport IT professionals and engineers faced in their offices.

At the end of the day, the button-down is a more casual version of the dress shirt, meaning you can use it to dress down your tie and jacket. Having said that, it isn’t usually a great fit for the silk tie or the suit. Flannel, knit, and more casual ties with sport coats, go all in and have fun. Picchione echoes this sentiment.

“The button-down shirt pairs perfectly with a navy blazer or tweed sport coat, with or without a necktie. It never looks quite right with a suit unless maybe it’s a soft, natural-shouldered garment, or perhaps if you’re a college professor. The expression of the shirt must match the expression of the tailored garment worn over it. A classic structured suit doesn’t usually work to my eye.”

Tips for wearing it today

So how do you wear it today? It first became popular among the Ivy League and affluent, which can give it a stuffy feel if you do it wrong (or right, if that is what you are going for). But like I always say: fashion is what you wear, style is how you wear it.

Let your personality and your personal aesthetic shine through. Wear it as a sport shirt, open over a Henley. Wear it with a knit tie and an unstructured sport coat for a killer dinner look. Or, tuck it in and layer a sweater over it for the ultimate dad ensemble for a holiday. Either way, this is about how you want to look.

“Your personal style should come through, and anyone should feel comfortable wearing a button-down shirt,” Picchione says. “They can be worn loose and oversized or super skinny and snug. They work when they are crisp and new or tattered and worn. To me, a young guy wearing a button-down shirt, navy blazer, and solid silk knit necktie always looks great, especially in comparison to the sea of performance golf polos that have become the de facto uniform of the modern man.”