With the possible exceptions of nudists, He-Man and Mark Zuckerberg, it’s fair to say that most men wear a lot of shirts. Whether it’s part of your 9-5 uniform or a date-night special, for a garment that sees so much use, it seems many guys still hold a pretty slender grasp on the fundamentals of shirt-wearing – i.e. how and when to tuck one in.

Even style icons like David Beckham have had their share of trouble in this department. In fact, the A-lister became so confused by shirt-tucking during one period in the noughties that he decided the safest course of action would be to wear his half in and half out – in theory, killing two sartorial birds with one stone. Did it work? Did it bollocks. But it’s a style that some on the Fashion Week fringes still occasionally trot out.

So let’s take a look at the foolproof shirt tucks every man should have in his repertoire.

When To Tuck A Shirt In

Before we delve into the various methods of shirt tucking (because yes, there is more to it than just stuffing the hem haphazardly into your trousers), it’s important to deem whether your chosen garment actually needs to be tucked in at all. Luckily, there’s a simple way of figuring this out.

The shape of a shirt’s hem is a good clue as to whether you can simply throw it on without any hassle, or whether you need to undo your fly.

Straight Hem

If the hem of your shirt is a uniform length all the way around it is fine to be worn untucked. In fact, it was probably made to be worn that way.

This effectively gives you carte blanche to simply pop it on, button it up and walk straight out the door. Don’t forget to put the rest of your clothes on though, because you can get arrested for that kind of thing.

Curved Hem

A curved hem with an elongated front and tail usually denotes that a shirt should be worn tucked. It’s that shape for a reason – the extra fabric allows for a greater range of movement while remaining tucked in.

However, these are more guidelines than hard and fast rules – meaning there are plenty of grey areas in between.

“As a rule of thumb, the more pronounced the curve, the less acceptable it is to wear untucked,” explains Dean Gomilsek-Cole, head of design at Jermyn Street master shirtmaker Turnbull & Asser. “Also, the cloth is an indicator as to whether it should be worn in a more casual way; for example a dress shirt, complete with pique front bib etc., should never be worn untucked.” Unless you’re deliberately going for the ‘drunk uncle at a wedding’ look, that is.

“A shirt needs to have the right shaped hem and length tails to look right worn out,” agrees our second Jermyn Street bespoke shirtmaker, Emma Willis. “[It works best] with shorter lengths and a gentler curved ‘speed’ or ‘American’ hem, or square tail.”

For example, Oxford shirts often come with a subtle curve in the hem and, being a more casual style, this works tucked and untucked depending on what look you’re going for. The same is true of flannel shirts, which often feature a curved hem but should never be tucked in – unless it’s the weekend and you’re doing a spot of DIY, in which case it’s compulsory.

Shirt Length

Aside from the curve of the hem, a shirt’s length can also guide whether it should be tucked in or not.

If your shirt is coming untucked at the back every time you sit down it’s probably fair to assume that it either shrunk in the wash, or is not supposed to be tucked in at all. Dress shirts tend to finish a little way down your thigh when you put them on – in that case, they should always be tucked. Ditto if people are stopping you in the street to ask where you got your dress from.

Types Of Shirt Tuck

Believe it or not, there are several ways of tucking your shirt in. The type of shirt, what you’re wearing it with and the look you’re going for will all determine which technique below is most suitable.

The Loose Tuck

This is the most basic way of tucking your shirt in and most likely the method you’ve been using since you were old enough to dress yourself for school. However, that’s not to say it doesn’t still have its uses.

The loose tuck is good for speed and ease; to get it right simply tuck the excess fabric at the hem of your shirt into the waistband of your trousers, keeping it even all the way round, before fastening your zip and buttons, and holding everything in place with your favourite belt.

The loose shirt tuck

The Military Tuck

The military tuck is one shirt-tucking method that once you start using, you’ll never desert. There’s nothing worse (subjectively, of course) than when the fabric of your shirt begins to bunch up around the front, becoming loose and unsightly. This method eliminates that problem altogether.

Tuck your shirt into your waistband, as you have been doing all these years, but rather than simply calling that a day and buttoning up, run your thumbs around the front to the sides of your waistband, smoothing any creases or bunching from the front of the shirt.

Next, pinch the fabric at each side and fold it back on itself to create a fitted look, ensuring that your shirt’s placket lines up with the zip on your trousers. Finally, stand back and admire your handiwork in the mirror.

Military Shirt Tuck Technique

The Half Tuck

The half tuck, as the name would suggest, involves having the front of your shirt tucked into your trousers, while the back hangs out loose. Yet despite rumours that this style is ‘approved’ by Ralph Lauren himself, the rest of us would probably be wise to give it a wide berth. Unless, of course, you want to come off looking like a university rugby player on a team night out.

The half shirt tuck

The Underwear Tuck

In spite of what the name suggests, the underwear tuck doesn’t involve stuffing your shirt into your underpants. It’s actually a layered tucking method that works nicely when there’s an undershirt involved.

First, tuck the excess fabric at the bottom of the undershirt into your boxers or briefs. Once you’ve taken a moment to admire yourself in the mirror, put your shirt and trousers on and tuck your shirt in as you usually would.

If you really want to take things to the next level you could opt for a military tuck on the final step.

The underwear shirt tuck

The Jacket Tuck

A good, sharp-fitting jacket can hide a multitude of sins – one being a baggy shirt.

“If your shirt is a quite full and you wear a jacket you can cheat a bit,” explains Emma Willis. “Pull the fullness back so it’s smooth at the front and hide the extra cloth at the back, under your jacket. Pull down well to tuck in.”

Obviously, you’ll want to keep your jacket on if you opt for this method.

How to tuck in a shirt - the jacket/blazer tuck

How To Keep Your Shirt Tucked In

Now that you’re suitably educated on the intricacies of the various tucking methods, you’ll want to ensure your shirt stays firmly in place throughout the day/evening. Thankfully, there are a number of ingenious ways to do just that.

Dress Shirt Stays

The functionality of a set of shirt stays (£18.00; sharp&dapper) is twofold: firstly, they help to keep your shirt firmly in place beneath your suit or tuxedo any time the dress code says ‘smart’; secondly, they act as an effective method of birth control, should you happen to meet someone at said event.

Yes, if there is even the slightest possibility that your trousers might come off in the presence of anyone other than yourself, these monstrosities should remain firmly at the back of the wardrobe.

But if you’re confident that the mouse will be staying in his house, you can use a pair to attach the tops of your socks to the hem of your shirt, securing it in place. N.B. this should happen underneath your trousers, never on top.

sharp&dapper Shirt Stays Classic in Black

Rubber Grip Tape

If the dress shirt stays don’t sound too appealing, the use of rubber grip tape is a trick favoured by tailors that could well make your life a lot easier.

These thin strips of sticky-back rubber can be stuck around the inside of your trousers’ waistband, stopping your shirt from coming untucked.

Just make sure when ordering ‘grip tape’ on Amazon you pick the purpose-made rubber stuff and not the skateboard variety, unless you want holes in your shirt and grazes on your waist.

Rubber Grip Tape on trouser waistband to keep your shirt tucked in

The Mystery Button

Those little buttons you find lurking on the inside of some trousers – turns out they’re more than just a decorative feature.

You can use the buttons on each side of the inside of your trousers to anchor your shirt in place once its tucked in by hooking the shirt material around and behind the button.

Shirt Tucking Dos And Don’ts

DO: Always tuck in any sort of dress shirt.

DON’T: Tuck in any shirt that has a straight hem.

DO: Assess whether or not a shirt should be tucked in based on how much of a curve it has at the hem.

DON’T: Ever emulate David Beckham’s ‘one tail in, one tail out’ look.

DO: Use a military tuck to achieve a smooth, crease-free shirt front.

DON’T: Wear shirt stays unless you’re positive you won’t be removing your trousers in the presence of company.