Alright, gents. Those of you who know the difference between a button up shirt and a button down shirt get a gold star. For those of you who don’t know the difference—or didn’t realize there was a difference—don’t worry. We were just as confused, and we’ll happily share our newfound knowledge with you.
Turns out, like other fashion rules, the truth about men’s shirts is sort of complicated. We’ll break it down for you this way:
Whether it’s a Charlie Harper-style cabana shirt or a tuxedo dress shirt, if a shirt uses buttons to close all the way up in the front, it’s a button-up shirt.
If a shirt buttons all the way up the front, and has a button on the point of each side of the collar that buttons into the top portion of the shirt, it’s a button-down shirt. The button-down shirt got its start on the polo fields of jolly old England. Polo players, sick of having their shirt collars flop up as they charged down the field, had the bright idea of fastening them down. Somehow the look caught on, and eventually came to symbolize a preppy, casually elegant style.
So a button-down shirt is a type of button up shirt. But not every button up shirt is a button-down shirt. Makes sense, right?
Now, for “The Rules.”
It is acceptable to wear a casual short-sleeved button-up shirt if:
1. You are sitting in an actual cabana.
2. You are from Miami, currently in Miami, and currently poolside, on the beach, or grilling something.
3. Your job requires it.
4. It is 1983.
5. You are in your 20s and a hipster.
6. You belong to a bowling league.
7. You are a woman and the shirt is a blouse.
*Editor’s note: We know there are cool versions of the short-sleeve button-up shirt out there, but it’s a fine line and, unless you know you can pull it off, it’s a risky fashion move. Short-sleeved button-ups should be somewhat fitted and worn untucked with jeans and casual shoes.
It is acceptable to wear a long-sleeved flannel button-up shirt if:
1. You are a lumberjack of some kind.
2. You are an aspiring mountain man.
3. You are moving heavy furniture in the fall.
4. Your job requires it.
It is ONLY acceptable to wear a button-down shirt if:
1. You work in a casual office or it’s casual Friday at your swanky office.
2. You’re out with the guys at an upscale sports bar
3. You’re on a date at a semi-casual sit-down restaurant
4. You’re going anywhere you want to look put together but not stuffy, or your plan is to look dressy without wearing a tie.
5. Your job requires it.
You must wear a button-up dress shirt if:
1. You plan to wear a tie
2. You are going to a job interview at any place from which you seek gainful employment.
3. You are attending a formal or semi-formal wedding or cocktail party.
4. You are having dinner at an upscale restaurant.
5. Your swanky office job requires it.
Wondering what you should and shouldn’t wear with a button-down shirt? Well, a tie is a real no-no. Also, you must not, under any circumstances wear a button-down shirt with a suit. You can wear a button-down shirt with a nice pair of jeans (tucked in, please, with a proper belt), with khakis, or with slacks, and you can pair it with a sport coat.