How to Unbutton and Still Look Buttoned-Up

Want to open up your shirt and cool off? Ask yourself these five questions first.

Staying buttoned-up during a heat wave is no easy task, but no man should be caught walking around with his cleavage out. Yes, you can absolutely undo a few buttons. No, you can’t undo every other one or any on your pants. There is a very specific way to pull off an open shirt. Ask yourself these five questions and you won’t go wrong.

Is My Shirt Tucked In?

If the answer to this question is yes and you’re wearing a shirt with a reasonably high second button—probably from a European brand—you can feel absolutely free to unbutton your top and second button. Leave it there. Otherwise you’ll look like a candy wrapper torn open at one end. The decision to let your chest (or chest hair) breath won’t look intentional. That’s a problem.

Am I Wearing an Undershirt?

There’s a follow-up question here: Is my undershirt disgusting? If it is, hide it from the world. If it isn’t, feel free to unbutton your top two buttons. Showing a bit of your crew neck (you should be wearing a crew neck unless you want people to see your undershirt) may not be appropriate at the office, but it’s no big deal at the bar. Just be sure that you’re not still wearing a jacket. You don’t want to send mixed messages.

Am I Wearing a Tie?

If you’re rocking the loose-tie-after-a-long-day open collar, more power to you. Presumably it’s afternoon or evening and you’ve earned it. Unfortunately, no one not named Peter Falk can pull off a loose tie with more than one button undone. The one exception – which makes the rule – is the loose bow tie. If you’ve got a loose bow tie, feel free to get extremely aggressive. You’re probably having a hell of a night.

Is My Shirt Patterned?

Patterns are great—expect to see micro-stripes everywhere come fall—but they demand structure. If you let a pattern fold over onto itself, parallel lines will become not-so-parallel lines and plaid will become chaos. The second button on your shirt should fall at your jugular notch, the hard indent between your collarbones. Keep it done and your shirt falls straight down your rib cage. Undo it and the placket will swing open, ruining the lines on your left side. Unless you’re actually holding an ax (and ideally even if you are) you do well to keep the check in check.

Am I Outside?

If the answer is yes, than you can feel free to open up. Your look, whether you’re wearing a suit or slacks or even jeans is now about casual comfort. You’re intentionally deconstructing your outfit, which is totally fine.

But it’s not a free for all. It’s never acceptable to unbutton your shirt halfway down and rock the New Jersey-made-man look. If you want to be really aggressive—and you’re in a park or near a pool—unbutton your shirt all the way. It’s better to look undressed than to look like you don’t know how clothes work.

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