Although the title of this text may lack the poetry of most sartorial musings (and remind you of an Aesop Fable); yet fittingly, there is a problem we aim to tackle--a small challenge we face several times every day : What to do about your shirt escaping your trousers.
There seems to be as many "solutions" to the problem as there are methods to get rid of a case of the hiccups, including a kind of garter-belt system - which we won't address here, as the mere thought of wearing a tether linking my socks to my shirt is an unbearable reflection. To avoid the issue, you may even forcefully tuck your shirt into your underwear or even try those strange magnetic inserts that fit on the underside of your belt...
I'd like to start with a confession : we've written in these very columns that a horizontal bottom buttonhole on a shirt is the hallmark of a quality product, as this small detail allows the shirt to stay tucked in more consistently during the day. But let's be realistic : this "purist" detail is nothing short of snobbery - because with or without a horizontal buttonhole, your shirt will try just as desperately to exit your trousers (usually at the least appropriate moment).
You've probably gotten used to the idea, given up on a solution and decided some questions in life have no answer.
To have your shirt looking impeccable all day long (especially if like me, you never wear belts or braces), you'll have to perform a 'manual tuck' two or three times a day at the very least, even if the inside belt of your bespoke trousers are tricked-out with a silicon band. It is a necessity which can make you regret opting for those incredible Neapolitan trousers, with multiple straps, over-straps and an asymmetrical buttoning system, which can take ten minutes of handiwork to "do up" properly (if you've bought those glorious Ambrosi or Dalcuore trousers, you may feel my pain).
There is, nevertheless, the possibility of two effective answers to the arduous rebel-shirt issue : one answer which I found in Italy at Maison Siniscalchi in Milan, and the other solution I discovered at Marol 1959 in Bologna.
Alessandro Siniscalchi devised a solution for a big, both literally and figuratively, customer. He presented the ultimate system, directly inspired by yesteryear's onesies for infants--integrated into the shirt. The shirt is worn around the family jewels and buttoned near the navel with zero possibility for the shirt tail to escape. This technique is probably not so comfy and may suffer a loss of sex-appeal upon undressing. Further, the design may not be practical if you must pee in haste (although you could get creative) but seems to be fail-proof nonetheless.
At Marol 1959 in Bologna, Manuela and her team also devised an ingenious system which is featured on all the brand's dress and business shirts. The system consists of a small, curved piece of fabric that underlaps the last two buttonholes at the bottom of the shirt. For me, this feature is by far the best I've tried in terms of usability and neat appearance at the front of the shirt after tucking.
While this design may not prevent your shirt from escaping 100 percent of the time, it will reduce the amount of bathroom drop-ins necessary to give your shirt yet another discreet and solid re-tuck. A small detail, maybe--but over the course of time, it becomes anything but.
There is a moral, though, to this small story : Buy shirts which are adapted to your body shape, since a shirt that conforms to the body is less likely to reject a good 'tucking-in'.