To tuck or not to tuck: one man’s battle with his shirt hem

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The purchase of a new shirt has led David Barnett to a new kind of wardrobe dilemma

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By David Barnett on

Having reached a certain age, I am in a quandary about shirts, and the tucking in, or not, thereof.

I’m talking about casual shirts, naturally, rather than the ones men buy for work, weddings or funerals. I think we can all agree that anything made to go under a suit for any formal occasion looks better tucked into the trousers.

But what of day-to-day shirts? My heart tells me to be free, and wild, and untucked. My head says that I would look better firmly secured by my waistband. But tucking in feels a little like giving up, while hanging out seems suspiciously like trying to hang on to youth receding in the rear-view mirror at an alarming pace.

I was in a shop a few weeks ago when I saw a shirt in just the shade of pale blue I’d been looking for. My wife asked if I was going to try it on; I wasn’t. It was a medium, and I’d had shirts from this shop before, so logic dictated I could save whole minutes by not messing about in the dressing room.

When I got it home and critically inspected myself wearing it in the mirror, three words offered themselves up: Wee Willie Winkie. It practically came down to my knees. All I needed was a candle and I could be off running through the town, upstairs and downstairs in my button-down Oxford collar nightgown.

The other shirt I’d bought from the same shop was of a suitable just-below-the-waist length to wear untucked. This one, no chance. For which, you are all entitled to call me an idiot for not bothering to try it on. 

But this was the catalyst for wondering whether shirts should be tucked in or left out. I consulted my well-thumbed A Well-Dressed Gentleman’s Pocket Guide by Oscar Lenius, but while it has much to say about the history and design of shirts (did you know that the detachable collar was apparently “invented” in 1820 when a Mrs Hannah Montague, so fed up of washing her husband’s shirts, cut off his collars to, in Lenius’s words, “minimise the daily drudgery”?) this tome is so respectable that it wouldn’t even countenance discussion of not tucking in a shirt.

All I needed was a candle and I could be off running through the town, upstairs and downstairs in my button-down Oxford collar nightgown

So then I turned to style bible GQ, who offered some crucial advice I had ignored when buying my blue shirt: to wit, if it has a straight hem all the way round, it lends itself to hanging free. But if it has tails, it should be tucked in. GQ does have this to say, though, on untucked tail shirts: “If the shirt fits you really well, it can work, but it’s a risky move, particularly if the shirt is not the right length. The ideal length for an untucked shirt is something that hits the middle of your back pocket or the zipper of your pants.”

Your back pocket. Not the backs of your knees. OK. However, use of the word “zipper” and the line “baseball games, bachelor parties and bar crawls are times in your life when you’ve earned the right to wear an untucked shirt” made me realise I was reading the American GQ website, so perhaps all advice regarding style should be taken with a pinch of salt. 

The rather dauntingly-titled Art of Manliness website has similar advice, going even further to say: “Wearing a shirt with tails untucked is not a forbidden look. But it is a juvenile one. With nothing else on the upper body, it makes you look like a teen rebel at a grown-up wedding.”

All of which is fine, useful advice. But it doesn’t address a major consideration when deciding whether to tuck or not: body shape. I am currently in one of my periodic phases where I don’t quite have the physique of a Greek demigod carved from marble. Being less washboard and more tumble dryer around the midriff can have major consequences when shirt wearing. Tucked in and your stomach is presented in sharp relief like some geographical survey map. Untucked and you risk a bit of lower-shirt billow. Problems, problems.

At a loss, I finally turned to Twitter, the font of all knowledge — well, half-baked opinions, anyway — when it comes to sartorial elegance.

Here are a few nuggets of advice:

“If jeans I’d go more casual and leave shirt untooked” (ah, the perils of autocorrect).

“Hang loose. Covers all kinds of sins” (belly-shaped sins, presumably).

“The only rule that matters is that it's ironed” (good call).

“Out. With skinny jeans” (says a man shaped rather hatefully like a pipe-cleaner).

“Depends on beer belly situation. Nobody wants the shirtfront overbite” (I learned a new phrase).

“I have a flowchart/decision tree – with or without jeans? Tie or waistcoat y/n? Formality of event? Did I eat too many pies?” (cripes, I thought I was overthinking this!)

And: “Tucked in or it looks like you're hiding something” (the only response from a woman).

I’m no nearer to solving the puzzle, but I have learned some valuable lessons, mainly involving hems and that time spent in a changing room is rarely wasted.

Four of the best shirts






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