How Do I Know if My Untucked Shirt Is Too Long?

Is there a limit on the length of an untucked shirt? I have many very good older shirts that were not made to wear untucked. Is it OK to wear them hanging out anyway? — Robert, Mandeville, La.

Ah, the joy of an untucked shirt! Who wants the uncomfortable constriction of all that material trapped around your waist? Untucking has been a signifier of casual cool since tucking was invented. (When was that? Back in the mists of time when the bottom part of shirts also served as men’s underwear.)

These days, between Casual Friday, the erosion of the office dress code, pandemic lockdowns and comfort dressing, untucking has become ever more popular. Yet it is not quite so simple as just pulling your shirt out of your pants (or skirt). To do untucking effectively, you have to take into consideration the impressions untucked shirts convey and the actual shape of the shirt. Especially those odd appendages known as shirttails.

Shirttails, those tonsil-like bits that hang down at the bottom of a button-up shirt, were meant to be tucked in, given their original function as the veil between one’s outerwear and one’s private bits.

In other words, they were not invented to be seen. That means bodily proportion is not taken into consideration when a designer or tailor considers the shirttail. And therein lies the rub, because proportion is the key to dress. It is also why even after the shirts-as-underwear exigency was no longer relevant, tucking continued.

Tucking in your shirt gives you a waist; it defines the separation between torso and legs. It conveys an impression of control and organization. Untucking changes that proportion and, in doing so, changes the body shape and the ethos. Hence the reason tucking has become a symbol of class, profession and the establishment — or the rebellion against and rejection of all of the above.

In recent years, however, numerous brands have begun to cater to those who want to have their cake and wear it, too. Which is to say: Go untucked, but with a neater effect.