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To tuck or not to tuck? Solving the age-old shirt dilemma

Can't decide whether to tuck your shirt in or not? Do both, like this style maven.

Can't decide whether to tuck your shirt in or not? Do both, like this style maven. Photo: Getty

A friend and I were discussing diets the other day, as you do.

We were having the “all the weight goes straight to my middle” conversation, and how hard it is to dress around that.

The current trend that promotes big bosoms and big butts is all very well, but if you don’t also have that tiny waist you run the risk of looking like Danny DeVito as The Penguin.

“I don’t want to be a middle-aged woman who has to wear a big shirt untucked over pants,” my friend said, as we fell about laughing in agreement, because we were already there.

If I had a waist, I’d tuck, sash and belt everything. I’d cinch a trench coat like Audrey Hepburn, tuck a t-shirt into jeans like Jane Birkin, put a belt over a jacket like Diane Keaton, and tuck a silk shirt into high-waisted flares like a Jackie Collins heroine.

Tucking is a very big styling trick within the fashion set. They tuck it all in, or they tuck the front of a shirt and not the back, or sometimes they artfully tuck half of the shirt in the front. It’s supposed to look nonchalant, like the way most men look accidentally.

I know what I think about tucking: if you’re slim, male or female, you should knock yourself out and tuck all the time.

Of course, there are times it can look daggy.

Take the short sleeved tropical print shirt. Do you wear it out like a politician at an Asia-Pacific conference? Or do you tuck it into white jeans, El Chapo-style, like UFC legend and world’s snappiest dresser Conor McGregor?

I have two male friends who are best friends and impeccable dressers, one who tucks a white shirt into jeans, the other than doesn’t because he is a bit bigger around the middle. They both look great.

But I have traditionally hated the un-tucked long-sleeved dress shirt worn out over jeans for men (throw in a pair of Oakley sunglasses and some square-toed dress shoes if you want to go peak bogan).

This gentleman can't make up his mind. Photo: Getty

This gentleman can’t make up his mind. Photo: Getty

I asked my 22-year-old sons their thoughts on whether or not to tuck.

“Hmm, its very contentious,” Sam said. “We disagree all the time. It really depends on who is doing the tucking.”

A tucked polo shirt could say “Donald Trump on the golf course” or “tour bus terribleness” but if trend-setting Pharrell rocks it, then it’s fine.

Jerry Seinfeld tucked a long sleeved shirt magnificently but my favourite is definitely the Obama look: white shirt tucked in, long sleeves rolled up.

Apparently, like it or not, the latest trend for men is the tucked t-shirt, worn with everything from jeans, to chinos, to shorts, with a shoestring belt.

It can look awesome on the very fashion forward; it also has the potential to go horribly wrong. Like everything in fashion, it’s all up to the wearer. Just don’t tuck it into your undies.

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