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I vividly remember consistently rebelling against tucking in my shirt.

It started at formal family events, untucking my shirt because the knee slides on the dance floor weren’t the same with your shirt tucked in.

It then progressed to School as the teachers would insist on keeping your shirt tucked in.

Looking back I’m not sure why I thought keeping my dress shirt untucked looked cooler than it did tucked in.

But as I got older and as I started to dress smarter it became clear that a tucked in dress shirt looks better than an untucked one. Then I faced another issue.

I found it difficult to keep it tucked in…

After all of those years rebelling against tucking in my shirt I now found it challenging to keep it tucked in.

Even the slightest movement would slowly untuck my shirt making me look scruffy in the process.

Believe it or not it’s a question most readers ask and to date (I can’t believe I’m saying this) it’s one of my most popular YouTube videos.

I wanted to break it down in article format for you, and show you how to keep your shirt tucked in.

How To Keep Your Shirt Tucked In

Yes, we’re actually doing this. I’m about to break down a few things to consider if that dress shirt of yours keeps untucking.

But before I do it’s important to realise that this is actually something that can have a big impact on your overall style.

Walking around with an untucked dress shirt or even a half tucked shirt can make you look like a rebellious schoolboy.

Menswear is all about the finer details and the way you tuck your shirt is a detail to seriously consider.

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1. Get A Shirt That Fits You

If the shirt you’re wearing is oversized you’re going to have a lot of excess fabric hanging over your trousers.

This is simply called a ‘Muffin Top’.

Again going back to the importance of details, excess fabric bunching up over the top of your trousers really isn’t a good look.

When you have an oversized shirt it also makes it easier to untuck with any kind of movement.

You want to go for something slim fitting, even if you’re a bigger guy. It needs to skim your body as this is going to not only look better it’s also going to make it easier to tuck in (and keep tucked in throughout the day).

Can’t find a shirt that fits you well off the rack? Take it to a tailor or alteration service to make it more slim fitting, or better yet, if you don’t have the time or you find a shirt that you love right off the rack but it still untucks, grab yourself a pair of Tucked Trunks boxer briefs. These boxer briefs are simple to use and help keep any shirt neatly tucked in whether it’s off the rack of altered.

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Image by Charles Tyrwhitt

2. Find A Shirt That’s Ideal In Length

Similar to the first point you want to wear a shirt that’s longer in length.

More casual shirts are typically manufactured to be shorter in the body making them ideal when left untucked, but dress shirts are typically made longer in length making it easier to tuck in.

You want to opt for something a little bit longer in length as it’s going to be easier to tuck in.

There’s always a debate of ‘when should you tuck in a shirt’. Personally if it’s a shorter length shirt you have the choice of keeping it untucked. Any shirt that’s long in length should be tucked in.

3. Tuck In Your Shirt

With the two points above considered tucking in your shirt (and keeping it tucked in) becomes a lot easier.

If the shirt isn’t slim fitting and if it isn’t ideal in length this is typically the main reason why your shirt consistently untucks throughout the day.

With all of the tucks below we recommend you do it with your trousers unfastened. Once tucked in, fasten your trousers and adjust the shirt if need be.

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Here are ways to tuck in your shirt.

The General Tuck

The simplest one, the one you’ve probably been doing for your whole life.

Simply unfasten your trousers and push the shirt into your trousers.

Nothing fancy, just try and tuck in the shirt evenly.

The Military Tuck

This tuck is great to use if your shirt hasn’t been altered or if it’s slightly bigger than it should be.

This is a great way to achieve the slim fitting look without taking your shirt to the tailor.

The way I do it is simple…

With my trousers unfastened I use my thumbs to push the fabric to the back of the shirt so the front should have no creases or excess fabric. Then using your thumbs again create a crease to tuck in the excess fabric in to the back of your trousers.

Here’s a visual demonstration.

military-tuck

I also demonstrate how in the video.

Shirt Stays

The other consideration is to use Shirt Stays. It’s something a lot of people don’t know exist but it’s a handy accessory if you still can’t seem to keep your shirt tucked in.

What are they you ask?

They’re simply elastic straps that connect the bottom of a dress shirt to the socks or feet.

Sharp & Dapper are a brand that we’ve spoken about before and something I personally recommend too if you want to take your shirt tucking game that step further.

shirt stays sharp and dapper shirt stays sharp and dapper shirt stays sharp and dapper

Go Tuck It In

So there we have it, a really simple process but something that’s important to pay attention too.

If you would have told me 7 years ago that I’d be writing an article on how to tuck a shirt in I would have called you crazy, but all of these finer details add up to help you improve your style.

Personally I focus on choosing a good shirt that fits well and is ideal in length, I also focus on a good fabric and then I’ll simply use the general tuck.

No excuses now.

Tuck those dress shirts in and make sure they stay tucked in throughout the day.

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