I know you should always wear a button-up shirt tucked into your trousers at the office or at an event like a wedding or funeral. But what about everywhere else? Is it ever OK to wear a shirt untucked?
Jeff, via contact form
Instead of racking your brain in an attempt to remember what your mum barked at you all those years ago, look to your shirt’s bottom hem for a cue on whether or not to tuck.
Shirts with a straight bottom hem – i.e. pretty much all shirts that aren’t dress shirts – are casual enough to be worn tucked or untucked. That’s Oxfords, plaid shirts, chambray shirts, corduroy shirts and anything else you’d be more inclined to wear with a pair of jeans or chinos than a tailored trouser. (Obviously anything heavier, like an overshirt, should never ever be tucked in unless you’re consciously channelling that Midwestern Trump supporter vibe.)
Shirts with a curved bottom hem, or tails, on the other hand, should always be tucked in. That’s mostly dress shirts, but you’ll find tails on casual shirts on occasion too. This isn’t so much a guideline as a style decree – leave your tails untucked and you’ll come a cropper, whatever the dress code.
It’s also worth bearing the length of the shirt in mind. As mentioned, straight-bottom-hem shirts can be worn either tucked in or left untucked – but feel free to disregard that rule completely if your shirt’s so long people mistake it for a dress.
Finally (and this is of particular importance with straight-bottom-hem shirts) consider the dress code. Where are you going? What will you be wearing your shirt with? If the answer’s work, and a suit, then keep your shirt tucked – no matter how straight its hem. If the answer’s a gig, and slim jeans and Chelsea boots, then feel free to let it all hang out – ideally with a black leather biker jacket.
Whatever you do, don’t ape David Beckham’s half-tuck *shudder*
— Cillian O’Connor, Features Editor