Ask Our Stylist: When is it appropriate to unbutton your shirt collar?
In an office environment that observes traditional professional dress standards, you should keep all buttons on your shirt buttoned at all times. This includes collar point buttons on your button-down shirt collar. Typically, in these settings, it is inexcusable to be seen without a jacket, let alone a tie, and note that your shirt must be buttoned to the top while wearing a tie.
In more laidback work environments where a jacket and a tie are not required, it is safe to have your collar button unfastened. This simple "popping of the collar" button produces a relaxed and casual look that also makes you appear more approachable.
Preserving a classy appearance is of utmost importance for a night out. When attending a dinner, it is safe to unbutton your collar button while simultaneously appearing smart and informal. It is considered to be in poor taste to undo any further buttons on your shirt placket, especially if there's a chance that you may sprinkle chest hair into your food.
When at a dance club or a bar, ordering a cocktail, you can both increase ventilation in your shirt and look good by unbuttoning a maximum of two buttons - your collar and the subsequent placket button. There are names for those who display undesirable behaviors such as unbuttoning three or more buttons on their shirts while attempting to attract a mate, and those names are not nice.
You make the rules here, and the temperature usually dictates those rules. For instance, if you're at a backyard BBQ and the sun is beaming on your crisp linen shirt, a maximum of two buttons (your collar and subsequent placket button) may be unfastened. This provides additional ventilation for your shirt and produces a classic summer look that has been mastered by every Hollywood star from Marlon Brando to Ryan Gosling.