How many shirt buttons should I leave undone? 1, 2, or more?

NOTE: Shirt shown above is Ledbury’s white fine twill with a mid-spread collar. They have a purposefully lowered second button which looks just-right when the top button is undone.

There has been an unignorable increase of men on television, red carpets, and in modeling shots wearing shirts with a LOT of their buttons unbuttoned. (Sidenote: Sometimes there are just no shirts at all.)

It’s enough male sternum to send a Victorian Lady crashing down into her chaise lounge.

It can also produce some good-natured ribbing:

https://youtube.com/shorts/FyrAswBwo8c?si=dqJQNgogun6i9O_n

Q: So how many buttons should you leave undone when wearing a dress shirt without a tie?

A: One. Ok maybe two (but only if you’re feeling frisky & risky)

Q: Not three?

A: No. Not three.

The increasingly common “three unbuttoned” move.
Shirts from Banana Republic, which is far from some high-risk experimental brand,
demonstrating just how far this trend has spread.

Seem a little stodgy? Old? Captain No-fun? Indeed.

But think about it this way…

Undoing shirt buttons is a lot like drinking

One is often a grand idea. (but when in doubt, wear a necktie.)
Two is getting risky, but can be fine depending on the circumstance.
Three or more (!?) and you’re drunk on your own “rizz.” And if that’s the case, you’re falling flat. Or to put it another way… your rizz has lost its fizz.

One is fine. Two is risky. Any more than that and your shirt’s drunk.
“First you take a drink. Then the drink takes a drink. Then the drink takes you.”
– F. Scott Fitzgerald (or probably not)

“So should I go with one unbuttoned or two? With two buttons undone, sometimes the placket drifts open and I feel uncomfortable. But with just one button undone, sometimes I can look like I just ripped off a necktie. It’s too stuffy. And I don’t want to look like that.”

First, I’ve been there.

But I also promise you no one notices as much about our style as we’d like to think. If you’re really hung up about it (again, I’ve been there) try finding a shirt brand that slightly lowers the stance of their 2nd button. Shirts with a slightly lowered 2nd button will look “just right” with the top button undone.

Ledbury does a slightly lowered 2nd button, standard.
Proper Cloth offers a lowered second button stance as an option, which you can choose while customizing.

What it looks like with (just!) one button undone on a shirt with a slightly lowered 2nd button.

And second, if you don’t want to invest in a bunch of new (expensive) shirts, and you think undoing just one button can look a little too stiff, there are still a lot of other things you can do to relax the “no tie” look, without unbuttoning the 2nd button and getting too chesty:

TL;DR:

Just the top button undone is the answer for most of us, most of the time.
Two buttons undone can be fine for many of us, some of the time.
Finding dress shirts with a slightly lowered second button can give you that “just right” look all of the time.
You can render the one button vs two debate moot by nailing the rest of the details:
- The shirt has a good collar that helps frame your face
- Good overall fit for the shirt/suit/blazer/etc.
- Wear slightly more visually appealing accessories but don’t go overboard
- Try a simple pocket square to take the place of a “missing” necktie

P.S. None of this really matters and nobody truly cares how many shirt buttons you leave undone. Least of all the editors of this particular goofy website which you’re reading right now.

P.P.S. Ledbury did not pay us to write or feature their shirts in this post. They’re just the shirts the Joe guy usually but not always wears, and he figured someone would ask.

P.P.P.S. The following posts may be additionally somewhat relevant: