4 Ways To Tuck In A Dress Shirt

Picture this:

You’re in the middle of a meeting getting ready for your big pitch. As you get up from your seat and go forward your dress shirt puffs out and comes untucked.

The worst part? YOU don’t notice… but everyone else does.

Guess what? That's become one hell of a distraction from your presentation. Your colleagues and boss simply don't take you seriously.

Do NOT let this happen to you.

Make shirt-tucking a non-issue for you permanently and learn these tips & techniques below that work like a charm.

When Should A Shirt Be Tucked In?

Was there ever a time you were getting dressed and suddenly thought – Is this shirt supposed to be tucked in?

Whenever in doubt, look at the bottom hem of your shirt. It not always obvious, but the length and style of the hem will signal the actual way of wearing the shirt.

If it’s a short hem that’s even all around the waist – as seen on t-shirts or polo shirts – tuck in the shirt. Remember that it’s likely to untuck itself if there’s not much to cover in the first place.

If it’s an uneven hem with tails in the front or back (sometimes longer in the front), it’s 100% for tucking in. These tails look like dangling, excess fabric for a reason – and not because they were originally stylish! They simply made it easier keep the shirt well-tucked.

Now if we’re talking about the type of shirt – this is where you have to remember how it’s traditionally worn. The following types should be tucked in all the time (although they don’t always have uneven hems these days):

• Long-sleeved dress shirts
• Chambray work shirts
• Flannel work shirts
• Wool “lumberjack” shirts
• Sports shirts with buttons at the front

And one other thing to consider is your environment or occasion. For any formal event, corporate function, wedding or dinner in a fancy restaurant – a tucked in shirt is part of the dress code (unless the host wants it casual). But if it turns out you plan to wear a guayabera, this is an exception.

Ground Rules Of A Well-Tucked Shirt

1. Shirt Length

You want a dress shirt with tails that extend at least 3 inches below the belt line. That makes sense since the longer your shirt is, the better its chances of staying tucked in and neat the whole time.

2. The Perfect Alignment

For your shirt to look its very best while tucked in, there has to be this imaginary straight line that’s formed when the shirt placket, the belt buckle and front seam of your trousers are all perfectly centered.

3. No Excess Material

Your top priority is to get rid of “extra” fabric that ruins the look of your tucked-in shirt. If you wear it the normal way but notice excess material – you can either take it to a tailoring shop or buy a new, custom made shirt.

Shirt Tucking Method #1 – The Basic Tuck

This first technique is something we’ve all used at some point in our lives. It’s almost the next thing that young boys learn after being told the concept of “tucked in.” It’s straightforward and easy to turn into a habit.

First you’re wearing your pair of pants, which you open and pull down before wearing the shirt. The next part is simply tucking it in – then pulling the pants back up. Close the zipper and button, tighten your belt. Finished.

However, this method isn’t super effective. It does an okay job but it’s not worth the risks of the getting untucked on its own – or even “ballooning” out at some point. If this way has been working out for you so far, I still recommend that you try the others (which aren’t complicated at all).

Shirt Tucking Method #2 – The Military Tuck

This is a widely used technique among men in the military. It takes the Basic Tuck and adds extra maneuvers to make it more efficient. But you’ll need some space in the room to get it right.

Start by wearing your pants unbuttoned. Then tuck your shirt in and close the zipper – but leave the button open. The next step is spreading your legs evenly to keep the pants from going down.

In this slightly awkward position, you’re going to “pinch” towards the back any excess fabric from the side seams. Use your thumb and index finger to do this on each side simultaneously. The end goal is a neatly folded pleat at the side of each hip (aligned with the armpit).

Once you’re done, close the button and even out all folds and creases. Then tighten the belt well for additional grip.

Shirt Tucking Method #3 – The Underwear Tuck

What I like about this technique is that it’s simple, logical and works every time. It eliminates the problems with wearing undershirts – which the other 2 methods don’t solve.

It’s all about the order of layering – undershirt, underwear, dress shirt & pants. Each shirt is tucked in under the item that follows it. Then all that’s left is wearing your belt and adjusting accordingly.

This method utilizes friction to hold both of the shirts in place. It prevents the undershirt from interacting with your dress shirt – one less pulling force that can make it go untucked.

Shirt Tucking Method #4 – Good Quality Shirt Stays

This happens to be my favorite technique. There’s no need for pinching, pushing down or pulling up with your hands. All that’s required is to insert and remove something once.

These awesome tools are called shirt stays – a.k.a. shirttail garters. They came out in the 19th century, changing the way men had to deal with stubborn tucked-in shirts forever. They use constant downward pressure to lock the shirttails in place.

There are 2 companies for me that make standout shirt stays – KK & Jay and Sharp & Dapper. It’s because of them that any guy can now move around as much as he needs to without shirt “limitations.” And their shirt stays are also very comfortable to wear – with all pressure applied into the shirt and socks only.

Whether you’re running, bending down, dancing or reaching for something… forget the chances of your shirt looking sloppy. They’re practically nil. But the chances of a clean-looking shirt that enhances your look? They’re pretty high.

Refer to this guide to wearing shirt stays properly. With this method there’s really nothing to lose. After you buy and clip them on – the rest of the job is done. Less time, less effort… and a big boost in confidence.