How to properly tuck your shirt (and keep it there)

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With the possible exception 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 special date, for a garment that’s used so much, it seems a lot of guys still have a pretty keen understanding of the fundamentals of shirt wearing – that’s ie how and when to get one in.

Even style icons like David Beckham have had their share of problems in this department. In fact, the A-lister got so confused by how to tuck a shirt during a period in the 2000s, he decided that 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? Is this screwed up. But it’s a style that some on the sidelines of Fashion Week still sport occasionally.

So let’s take a look at some surefire ways to tuck in a shirt that every man should have in his repertoire.

When to tuck in a shirt

Before we dive into the different shirt-folding methods (because yes, there’s more than just stuffing the hem randomly into your pants), it’s important to determine if the garment you’ve chosen actually needs to be tucked in. Fortunately, there is an easy way to figure this out.

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The shape of a shirt’s hem is a good clue as to whether you can just pull it on without any problem, or if you need to undo your fly.

Straight hem

If your shirt hem is a uniform length all the way around, it’s a good idea to wear it loose. In fact, it was probably meant to be worn that way.

This effectively gives you carte blanche to just put it on, button it up and go straight out the door. Remember to put on the rest of your clothes because you can get arrested for this sort of thing.

Curved hem

A curved hem with an elongated front and tail usually indicates that a shirt should be worn tucked in. It’s that shape for a reason – excess fabric allows for a greater range of motion while staying tucked in.

However, these are more guidelines than hard and fast rules, meaning there is a lot of gray area in between.

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“As a general rule, the steeper the curve, the less acceptable it is to wear loose,” says Dean Gomilsek-Cole, design manager at Jermyn Street master blouse, Turnbull & Asser. “In addition, the fabric is an indicator of whether it should be worn more casually; for example, a dress shirt, with a piqué plastron, etc., should never be worn un-tucked. Unless you deliberately go for the ‘drunk uncle at a wedding’ look, that is to say.
“A shirt has to have the right hem shape and tail length to look well worn,” agrees our second tailored blouse from Jermyn Street, Emma Willis. “[It works best] with shorter lengths and a softer curved “speed” or “american” hem, or a square tail. “
For example, Oxford shirts often have a subtle curve in the hem and, being a more casual style, they work tucked in or tucked in depending on the look you are going for. The same goes for flannel shirts, which often have a curved hem but should never be tucked in – unless it’s the weekend and you’re doing a bit of DIY, in which case it’s mandatory.

Shirt length

Besides the curve of the hem, the length of a shirt can also indicate whether it should be tucked in or not.

If your shirt unfolds at the back every time you sit down, it’s probably fair to assume that it shrunk in the wash or isn’t meant to be tucked in at all.

Dress shirts tend to end up a bit down your thigh when you put them on – in which case they should always be tucked in. Ditto if people stop you in the street and ask you where you got your dress from.

Types of shirts

Believe it or not, there are many ways to tuck your shirt in. The type of shirt, what you wear it with and the look you are going for will determine the most appropriate technique below.

1. The loose fold

It’s the easiest way to tuck your shirt in and probably the method you’ve been using since you were old enough to dress for school. However, that does not mean that it does not yet have its uses. The loose pleat is great for informal situations where you still want to have a semi-polished look.

  • Start with an ironed shirt or polo shirt that doesn’t fit you.
  • Tuck your shirt into your waistband, starting from the back to the front of your pants. It doesn’t have to be perfect, but the point is to tuck the entire bottom of your shirt into your pants.
  • Finish by shrugging your shoulders or gently raising your arms to create a fuller look.

Loose shirt

2. The military withdrawal

Military fold is a shirt folding method that once you start using you will never desert. There is nothing worse (subjectively, of course) than when the fabric of your shirt begins to pack in the front, becoming loose and unsightly. This method completely eliminates this problem.

  • Tuck your shirt into your waistband like you’ve done all these years, but rather than just calling it a day and buttoning it up, wrap your thumbs around the front on the sides of your waistband, smoothing out any pleats or puckering the front of the shirt.
  • Then pinch the fabric on each side and fold it back on itself to create a fitted look, making sure your shirt placket lines up with the zipper on your pants.
  • Finally, take a step back and admire your work in the mirror.

Military shirt folding technique

3. The Half-Tuck

The half-pleat, as the name suggests, involves the front of your shirt tucked into your pants, while the back is loose. Still, despite rumors that this style is “endorsed” by Ralph Lauren himself, the rest of us would probably be wise to give it a big place. Unless, of course, you want to look like a college rugby player at a team night out.

  • Loosely tuck the front of your shirt into your belt.
  • Shrug your shoulders to soften the look without unfolding the front of your shirt.
  • Smooth out the creases and make sure the rest of the shirt isn’t tucked in to the sides or back, but hangs loose.

The half-shirt fold

4. The Tuck underwear

Despite what the name suggests, the underwear doesn’t involve tucking your shirt into your boxer shorts. It’s actually a layered folding method that works well when an undershirt is 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 on your shirt and pants and tuck your shirt in as usual.
  • If you really want to take things to the next level, you can opt for a military retreat on the last stage.

Tuck shirt underwear

5. The Tuck jacket

A good, well-fitting jacket can hide a multitude of sins, one being a loose shirt. “If your shirt is loose enough and you’re wearing a jacket, you can cheat a bit,” says Emma Willis.

  • “Pull the volume back so it’s smooth in the front and hide the extra fabric in the back, under your jacket.
  • Pull well down to enter. Obviously, you’ll want to keep your jacket on if you go for this method.

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

How to keep your shirt tucked in

Now that you are familiar with the intricacies of the different folding methods, you’ll want to make sure your shirt stays firmly in place throughout the day / evening. Fortunately, there are a number of neat ways to do this.

1. Dress shirts

The functionality of a set of shirts (£ 18.00; sharp & dapper) is twofold: first, they help keep your shirt firmly in place under your suit or tuxedo whenever the dress code says “smart”; second, they act as an effective method of birth control, if you meet someone at this event.

Yes, if there is the slightest possibility that your pants will come off in the presence of someone other than yourself, these monstrosities should stay firmly at the back of the closet.

But if you’re sure the mouse will stay in its house, you can use a pair to tie the top of your socks to the hem of your shirt, securing it in place. Be careful, this must happen under your pants, never on the top.

The sharp & dapper shirt remains classic in black

2. Rubber adhesive tape

If shirt scraps don’t look too appealing, using rubber duct tape is a tailor-favored tip that just might make your life easier.

These thin adhesive rubber bands can be stuck to the inside of your pants waistband, preventing your shirt from unfolding.

Just make sure that when you order “grip tape” from Amazon, you choose the specially designed rubber and not the skateboard variety, unless you want holes in your shirt and scrapes at the waist.

Rubber grip tape on the waistband of the pants to keep your shirt tucked in

3. The mystery button

Those little buttons that you find hidden inside some pants – turn out to be more than just a decorative item.

You can use the buttons on either side of the inside of your pants to anchor your shirt in place when tucked in by hooking the shirt fabric around and behind the button.

Do’s and Don’ts

TO DO: Always tuck into any sort of dress shirt.

NOT: Tuck in any shirt that has a straight hem.

TO DO: Evaluate whether a shirt should be tucked in or not based on the curve of its hem.

NOT: Always imitate David Beckham’s “tail in, tail out” look.

TO DO: Use a military pleat for a smooth, wrinkle-free shirt front.

NOT: Wear shirts unless you are sure you will not remove your pants in the presence of your company.

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