You probably started tucking in your shirt as early as you can remember. Maybe it was for picture day or Easter Sunday mass, usually because mother said so.
In any case, it’s something we rarely think about, but there is a time and a place for a proper shirt tuck, and there are several different ways to do it depending on where you are, the situation and level of formality or casualness that you want to give off.
And so this article is a complete guide on how and when to tuck in your shirt, and perhaps most importantly, how to keep your shirt tucked in all day long.
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HOW TO TUCK IN YOUR SHIRT
These are all serviceable shirt tucks that you will want to know about and have at your disposal. Let’s start things off with the half tuck.
The Half Tuck (Front Tuck)
The half tuck also known as the front shirt tuck exudes a carefree nonchalance. It’s most appropriate when you’re keeping it casual. A proper half tuck can demonstrate that your style game is on point.

Think of the half tuck as business in the front and party in the back. Visually the front of the shirt is tucked in to your trousers while the back hangs loose. There’s a bit of sprezzatura (sprez·za·tu·ra — a studied carelessness) involved with the half tuck.
With a little bit of confidence, any man can pull of this stylish shirt tuck. The half tuck also includes the quarter tuck which is the same except one side of your shirt tail is tucked into the front of your pants as opposed to both.
The Full Tuck
A full tuck is the standard shirt tuck that you learned as a child and still use till this very day. It’s the method that business professionals use too. Typically you fully tuck in your shirt when wearing a dress shirt with dress pants or any type of more formal clothing.

Although, it’s worth noting that there are no hard and fast rules here, as men will often tuck their more casual oxford cloth button down shirts into their jeans or chinos for example.
The Bottom Line:
The full tuck is reserved for any occasion where you aim for a presentable, well put-together appearance.
The Military Shirt Tuck
The military shirt tuck is a technique that helps to for your full tuck to appear more presentable. It’s a good short term solution for men who want to conceal the excess fabric billowing around the waist.
Often times men wear dress shirts that are simply a size or two too big and so the military tuck can come in handy in these situations. To do it, you simply take the extra fabric at the sides of the shirt, fold it, and wrap it around the back.

Although this shirt tuck isn’t bulletproof, it’s a good temporary solution, especially when you’re wearing a blazer. And so no one is really going to notice that you’ve wrapped the excess fabric around the back and the front will appear clean and streamlined.
The Underwear Tuck
This is one of my go-to ways that I tuck in my shirt. With the underwear tuck, you want to be wearing an undershirt (not a t-shirt) under your button up shirt. It’s called the underwear tuck because you tuck your undershirt into your underwear and then tuck your dress shirt into your trousers as you normally would.

The benefit of the underwear tuck is that by tucking in your undershirt into your underwear, it creates a separation of undershirt and dress shirt between your boxers or boxer briefs. It allows for a cleaner shirt tuck because of that separation of fabric, and so you will avoid the dreaded muffin top appearance.
Additionally, the friction helps to keep the shirt more securely tucked in even when you move your arms and body throughout the day.
Now that we’ve covered the various ways to tuck in your shirt, here are the many different reasons for when to untuck and tuck in your shirt.
WHEN TO TUCK IN YOUR SHIRT
Curved Shirt Tails

For the most part, button ups with a flat bottom hem should be untucked, but as a rule, shirts with a visible curve around the bottom should be tucked in. These shirts are usually longer and it’s clear when you’re wearing a shirt with a curved hem.
Wearing A Dress Shirt
You always want to tuck in a dress shirt. Dress shirts are formal and anytime you’re adhering to a formal dress code, your best bet is to tuck in your shirt. One of the most common style sins that men commit is wearing a dress shirt untucked.
It particularly plagued many men who were into the clubbing scene in the 2000s. Speaking of, wearing dress shirts with jeans are a bad look. Don’t do it.
Longer Shirt Length

In addition to the style of shirt, the length of the shirt will determine if you may want to tuck it in. If the shirt tails cover your butt and go well past the crotch area, the shirt should definitely be tucked in.
Smart Casual Style
This is how you can casually tuck in your shirt. If you’re going for more of a smart, yet still casual vibe then you might want to tuck in well fitting polo, t-shirt or henley shirt into a pair or chinos or more formal trousers. This gives off sort of a high-low aesthetic that can look super sharp and put-together.

It takes a confident man to pull off this type of style, but in my opinion it looks stellar.
Formal Events
It goes without saying, but any type of formal event where a suit and tie is required, you’ll want to tuck in your shirt. An untucked shirt under a suit jacket and trousers is sloppy no matter how fashion forward you may think you are.

Keep in mind an untucked shirt under a blazer with more casual jeans or chinos and no tie can be done, but it’s more of an advanced style move, so be warned.
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WHEN TO UNTUCK YOUR SHIRT
Flat Bottom Hem

First, your shirt style is going to dictate whether or not you tuck in or untuck your shirt. As a general rule of thumb, shirts with a flat bottom hem are supposed to be worn untucked. If the shirt runs well past your butt and crotch area, then most likely it is too big for you and you may want to size down if possible.
Going For Casual Style
If you’re going for casual vibes, for example jeans and a t-shirt, then it’s highly recommended to untuck your shirt. Because anytime you tuck your shirt in, you will always appear more dressed up.
Shorter Shirt Length
Usually a shirt that’s meant to be untucked will end around mid-fly, plus it will be difficult to keep a shirt tucked in that’s too short anyway. And so, certain types of shirts are usually better suited to be worn untucked, eg. basic t-shirts, henleys, light cardigan sweaters.
Now that we’ve covered when to tuck in your shirt, let’s get into how to keep your shirt tucked in longer.
HOW TO KEEP YOUR SHIRT TUCKED IN
The dreaded billowing of the waist is a common problem that plagues millions of men worldwide, but here are two effective methods to help you keep your shirt tucked in throughout the day.
Wear Pants With A Higher Rise
Wearing pants with a higher rise will always allow for a cleaner shirt tuck.

With high rise trousers, there’s more room for the shirt to be tucked in, unlike with low rise pants, where less of the shirt gets tucked in. And more often than not, the shirt come undone as you move around throughout the day. But with pants that have a higher rise, your shirts will stay tucked in easier and effortlessly.
Use Shirt Stays
This method may not be the most comfortable or convenient, but it is one of the best ways to keep your shirt tucked all day long. Shirt garters aka shirt stays are not explicitly mentioned in the uniform regulations of any of the branches of the Armed Forces of the United States, but this only means that it’s one of the military’s best-kept secrets.

Shirt stays consist of stretchy elastic Y bands with clips that attach to the shirt tails all the way down to your socks. This ensures that your shirt stays tucked in all day long without fail. It’s the single most best way to keep your shirt tucked in, in addition to keeping your socks up and so it serves two functions.
As great as these are, there are some drawbacks. They can be uncomfortable when worn for long periods and are a pain when going to the bathroom.
WHAT SHIRTS TO KEEP TUCKED IN
These shirts are traditionally worn tucked in, but there are times that you may want to untuck these and so some may appear under both shirts to tuck and shirts to untuck.
- Dress shirts (always)
- Oxford Cloth Button Downs (sometimes)
- Polo (sometimes)
- Short sleeve button up (sometimes)
- Flannel (sometimes)
- Chambray (sometimes)
- Linen (sometimes)
- T-shirts and short sleeve henleys (sometimes)
WHAT SHIRTS TO KEEP UNTUCKED
- Jackets and hoodies (always)
- Cardigan (always)
- Polos (sometimes)
- T-shirts & henleys (sometimes)
- Oxford Cloth Button Downs (sometimes)
- Tropical print (depends on your style)
- Short sleeve button up (almost always)
- Tank tops (mostly)
WRAPPING UP
In this comprehensive shirt tuck guide we touched on 4 different ways to tuck in your shirt, several reasons for tucking in and keeping your shirt untucked, how to keep your shirt tucked in all day and shared some style inspiration on how to wear the different shirt tucks.
I think that’s just about everything you’ll want to know about tucking in your shirt. That’s it for now, I hope you got some value out of this!
WHAT SHIRT TUCK METHOD IS YOUR GO-TO?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to seeing you in there.
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Great stuff. Everyone needs that one friend who tells you what works and what doesn’t work.
Thanks for reading Jason! True, it doesn’t hurt to have that friend in your life. Do you have that friend or are you that friend? Hah.
where are your brown trousers from?
They’re custom from Black Lapel. Here’s the exact cut and pattern: https://shrsl.com/1ugfr.